MiMeDB: Showing metabocard for Bilirubin (MMDBc0000328)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:28:49 UTC

Update Date

2024-09-27 20:55:55 UTC

Metabolite ID

MMDBc0000328

Metabolite Identification

Common Name

Bilirubin

Description

Bilirubin is a yellow bile pigment that is a degradation product of heme. It occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from the destruction of aged or abnormal red blood cells. Bilirubin has been found in all vertebrates and in certain plants including Strelitzia nicolai (PMID: 28573242 ). Bilirubin levels in humans are elevated in certain diseases such as jaundice and liver disease and it is responsible for the yellow color of bruises and the yellow discoloration in jaundice. Bilirubin breakdown products, such as stercobilin, cause the brown color of feces. A different breakdown product, urobilin, is the main component of the straw-yellow color in urine. Bilirubin consists of an open chain of four pyrroles (tetrapyrrole). It is formed by oxidative cleavage of a porphyrin in heme, which leads to biliverdin, a green tetrapyrrolic bile pigment that is also a product of heme catabolism. Biliverdin is then reduced to bilirubin via biliverdin reductase. After conjugation with glucuronic acid, bilirubin can be excreted in the urine. Bilirubin is structurally similar to the pigment phycobilin used by certain algae to capture light energy, and to the pigment phytochrome used by plants to sense light. Elevated bilirubin levels in humans are associated with Crigler-Najjar syndrome type I, which is an inborn error of metabolism. Crigler-Najjar syndrome is a rare genetic disorder characterized by an inability to properly convert and clear bilirubin from the body. Affected individuals cannot convert unconjugated bilirubin to the conjugated form because they lack a specific liver enzyme required to break down (metabolize) bilirubin. Since they cannot convert bilirubin, they develop abnormally high levels of unconjugated bilirubin in the blood (hyperbilirubinemia). Crigler-Najjar syndrome is caused by mutations in the UGT1A1 gene. The hallmark finding of Crigler-Najjar syndrome is a persistent yellowing of the skin, mucous membranes and whites of the eyes (jaundice). Elevation of both alanine aminotransferase and bilirubin levels in serum or plasma can be indicative of serious liver injury. High levels of bilirubin are indicative of jaundice, which is easily recognizable due to a yellowing of the skin and eyes. Bilirubin is also an antioxidant. Bilirubin's antioxidant activity may be particularly important in the brain, where it prevents excitotoxicity and neuronal death by scavenging superoxide during N-methyl-D-aspartic acid neurotransmission (PMID: 31353321 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303182019232D          

 43 46  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4520   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 37  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 39  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 37  2  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
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 21 16  2  0  0  0  0
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 39 40  1  0  0  0  0
 40 42  1  0  0  0  0
 42 41  2  0  0  0  0
 42 43  1  0  0  0  0
M  END

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
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  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
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 26 64  1  0
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 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END


  Mrv1652303182019232D          

 43 46  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 37  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 39  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 37  2  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 16 27  1  0  0  0  0
 18 16  1  0  0  0  0
 21 16  2  0  0  0  0
 38 17  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  2  0  0  0  0
 19 21  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
 25 26  1  0  0  0  0
 28 34  1  0  0  0  0
 29 28  1  0  0  0  0
 38 28  2  0  0  0  0
 31 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 39 40  1  0  0  0  0
 40 42  1  0  0  0  0
 42 41  2  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000328

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

> <INCHI_IDENTIFIER>
InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-

> <INCHI_KEY>
BPYKTIZUTYGOLE-IFADSCNNSA-N

> <FORMULA>
C33H36N4O6

> <MOLECULAR_WEIGHT>
584.6621

> <EXACT_MASS>
584.263484904

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
66.1582703894841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.119106452999999

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.630728870728111

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.027490824017337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.754561928374644

> <JCHEM_POLAR_SURFACE_AREA>
164.37999999999997

> <JCHEM_REFRACTIVITY>
168.89600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bilirubin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856   -0.8971   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -4.0694   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373    0.5387    0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6784    1.0880    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2168    3.9181   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0050    3.9725   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9904    2.2043    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7853    3.6976   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    2.7100   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889    2.1286   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2984    1.1357   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.480  -2.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.465  -3.953   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.940  -2.488   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.956  -3.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.421  -4.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.710  -4.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.092   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.759   0.165   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.253   0.485   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.499   2.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.819   4.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.529   1.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.061   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.687   3.066   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.758   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.465  -3.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.481  -2.488   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.941  -2.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.956  -3.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.421  -4.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.711  -4.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.711  -6.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.711  -9.478   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -4.429   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.759   0.165   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.529   1.498   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.061   1.659   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.499   2.642   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.819   4.149   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.284   4.625   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.253   0.485   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       2.092   2.016   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.758   2.786   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.710  -6.398   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.710  -9.478   0.000  0.00  0.00           O+0
CONECT    1   37    3    4                                                  
CONECT    2    6    3   27                                                  
CONECT    3    1    2                                                       
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    2    4   39                                                  
CONECT    7   15    9   10                                                  
CONECT    8   37    9   12                                                  
CONECT    9    7    8                                                       
CONECT   10    7   12   11                                                  
CONECT   11   10                                                            
CONECT   12    8   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    7                                                            
CONECT   16   27   18   21                                                  
CONECT   17   38   18   19                                                  
CONECT   18   16   17                                                       
CONECT   19   17   21   20                                                  
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   25                                                       
CONECT   24   25                                                            
CONECT   25   23   24   26                                                  
CONECT   26   25                                                            
CONECT   27    2   16                                                       
CONECT   28   34   29   38                                                  
CONECT   29   28   31   30                                                  
CONECT   30   29                                                            
CONECT   31   29   35   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   28   35                                                       
CONECT   35   31   34   36                                                  
CONECT   36   35                                                            
CONECT   37    1    8                                                       
CONECT   38   17   28                                                       
CONECT   39    6   40                                                       
CONECT   40   39   42                                                       
CONECT   41   42                                                            
CONECT   42   40   41   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

COMPND    HMDB0000054
HETATM    1  C1  UNL     1      -9.381   3.399  -0.124  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.393   2.718   0.011  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.236   1.922   0.168  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.355   1.895  -0.888  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.513   2.625  -2.170  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.222   1.021  -0.534  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.254   0.706  -1.350  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.141  -0.163  -1.018  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.859   0.108  -1.387  1.00  0.00           N  
HETATM   10  C9  UNL     1      -1.035  -0.961  -1.050  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.330  -0.999  -1.512  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.586  -0.897  -0.843  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.319   0.294  -0.918  1.00  0.00           N  
HETATM   14  C12 UNL     1       3.508   0.153  -0.342  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.665   1.032  -0.299  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.750   2.274   0.005  1.00  0.00           C  
HETATM   17  N3  UNL     1       3.602   3.060   0.395  1.00  0.00           N  
HETATM   18  C15 UNL     1       4.030   4.393   0.625  1.00  0.00           C  
HETATM   19  O1  UNL     1       3.333   5.393   0.980  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.451   4.427   0.377  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.312   5.654   0.511  1.00  0.00           C  
HETATM   22  C18 UNL     1       5.882   3.180   0.011  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.250   2.929  -0.321  1.00  0.00           C  
HETATM   24  C20 UNL     1       7.875   1.870  -0.668  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.556  -1.126   0.124  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.708  -1.727   0.862  1.00  0.00           C  
HETATM   27  C23 UNL     1       2.372  -1.815  -0.175  1.00  0.00           C  
HETATM   28  C24 UNL     1       2.232  -3.266   0.084  1.00  0.00           C  
HETATM   29  C25 UNL     1       2.780  -4.069  -1.095  1.00  0.00           C  
HETATM   30  C26 UNL     1       2.634  -5.512  -0.862  1.00  0.00           C  
HETATM   31  O2  UNL     1       1.576  -6.099  -1.025  1.00  0.00           O  
HETATM   32  O3  UNL     1       3.767  -6.230  -0.437  1.00  0.00           O  
HETATM   33  C27 UNL     1      -1.854  -1.870  -0.455  1.00  0.00           C  
HETATM   34  C28 UNL     1      -1.483  -3.153   0.153  1.00  0.00           C  
HETATM   35  C29 UNL     1      -0.968  -2.951   1.554  1.00  0.00           C  
HETATM   36  C30 UNL     1      -2.008  -2.404   2.452  1.00  0.00           C  
HETATM   37  O4  UNL     1      -2.831  -3.180   3.052  1.00  0.00           O  
HETATM   38  O5  UNL     1      -2.138  -1.054   2.673  1.00  0.00           O  
HETATM   39  C31 UNL     1      -3.175  -1.393  -0.433  1.00  0.00           C  
HETATM   40  C32 UNL     1      -4.325  -2.231   0.002  1.00  0.00           C  
HETATM   41  N4  UNL     1      -5.437   0.539   0.771  1.00  0.00           N  
HETATM   42  C33 UNL     1      -6.678   1.088   1.202  1.00  0.00           C  
HETATM   43  O6  UNL     1      -7.175   0.843   2.356  1.00  0.00           O  
HETATM   44  H1  UNL     1     -10.217   3.918  -0.149  1.00  0.00           H  
HETATM   45  H2  UNL     1      -9.005   3.972  -1.301  1.00  0.00           H  
HETATM   46  H3  UNL     1      -8.990   2.204   1.175  1.00  0.00           H  
HETATM   47  H4  UNL     1      -6.785   3.698  -1.968  1.00  0.00           H  
HETATM   48  H5  UNL     1      -5.508   2.710  -2.690  1.00  0.00           H  
HETATM   49  H6  UNL     1      -7.189   2.129  -2.887  1.00  0.00           H  
HETATM   50  H7  UNL     1      -4.298   1.136  -2.383  1.00  0.00           H  
HETATM   51  H8  UNL     1      -1.580   0.992  -1.841  1.00  0.00           H  
HETATM   52  H9  UNL     1       0.413  -2.049  -2.135  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.375  -0.352  -2.510  1.00  0.00           H  
HETATM   54  H11 UNL     1       1.987   1.176  -1.350  1.00  0.00           H  
HETATM   55  H12 UNL     1       5.623   0.551  -0.586  1.00  0.00           H  
HETATM   56  H13 UNL     1       2.639   2.699   0.495  1.00  0.00           H  
HETATM   57  H14 UNL     1       6.971   5.777  -0.364  1.00  0.00           H  
HETATM   58  H15 UNL     1       6.918   5.552   1.445  1.00  0.00           H  
HETATM   59  H16 UNL     1       5.696   6.555   0.631  1.00  0.00           H  
HETATM   60  H17 UNL     1       7.953   3.826  -0.283  1.00  0.00           H  
HETATM   61  H18 UNL     1       7.539   0.898  -0.801  1.00  0.00           H  
HETATM   62  H19 UNL     1       8.977   1.958  -0.888  1.00  0.00           H  
HETATM   63  H20 UNL     1       5.434  -0.941   1.116  1.00  0.00           H  
HETATM   64  H21 UNL     1       4.378  -2.186   1.847  1.00  0.00           H  
HETATM   65  H22 UNL     1       5.261  -2.500   0.276  1.00  0.00           H  
HETATM   66  H23 UNL     1       2.944  -3.519   0.943  1.00  0.00           H  
HETATM   67  H24 UNL     1       1.290  -3.644   0.386  1.00  0.00           H  
HETATM   68  H25 UNL     1       2.277  -3.780  -2.008  1.00  0.00           H  
HETATM   69  H26 UNL     1       3.890  -3.873  -1.152  1.00  0.00           H  
HETATM   70  H27 UNL     1       4.661  -5.724  -0.302  1.00  0.00           H  
HETATM   71  H28 UNL     1      -2.387  -3.823   0.279  1.00  0.00           H  
HETATM   72  H29 UNL     1      -0.790  -3.739  -0.468  1.00  0.00           H  
HETATM   73  H30 UNL     1      -0.085  -2.252   1.604  1.00  0.00           H  
HETATM   74  H31 UNL     1      -0.684  -3.937   1.968  1.00  0.00           H  
HETATM   75  H32 UNL     1      -2.020  -0.302   2.034  1.00  0.00           H  
HETATM   76  H33 UNL     1      -4.207  -3.301  -0.396  1.00  0.00           H  
HETATM   77  H34 UNL     1      -4.500  -2.322   1.060  1.00  0.00           H  
HETATM   78  H35 UNL     1      -5.220  -1.880  -0.589  1.00  0.00           H  
HETATM   79  H36 UNL     1      -4.815  -0.053   1.351  1.00  0.00           H  
CONECT    1    2    2   44   45
CONECT    2    3   46
CONECT    3    4    4   42
CONECT    4    5    6
CONECT    5   47   48   49
CONECT    6    7    7   41
CONECT    7    8   50
CONECT    8    9   39   39
CONECT    9   10   51
CONECT   10   11   33   33
CONECT   11   12   52   53
CONECT   12   13   27   27
CONECT   13   14   54
CONECT   14   15   25   25
CONECT   15   16   16   55
CONECT   16   17   22
CONECT   17   18   56
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   57   58   59
CONECT   22   23
CONECT   23   24   24   60
CONECT   24   61   62
CONECT   25   26   27
CONECT   26   63   64   65
CONECT   27   28
CONECT   28   29   66   67
CONECT   29   30   68   69
CONECT   30   31   31   32
CONECT   32   70
CONECT   33   34   39
CONECT   34   35   71   72
CONECT   35   36   73   74
CONECT   36   37   37   38
CONECT   38   75
CONECT   39   40
CONECT   40   76   77   78
CONECT   41   42   79
CONECT   42   43   43
END

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856   -0.8971   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -4.0694   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373    0.5387    0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6784    1.0880    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2168    3.9181   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0050    3.9725   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9904    2.2043    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7853    3.6976   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    2.7100   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889    2.1286   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2984    1.1357   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END

Synonyms

Value	Source
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid	ChEBI
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	ChEBI
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid	ChEBI
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione	ChEBI
Bilirubin(Z,Z)	ChEBI
Bilirubin-ixalpha	ChEBI
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionate	Generator
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate	Generator
Bilirubin ixalpha	HMDB
(4Z,15Z)-Bilirubin ixa	HMDB
(Z,Z)-Bilirubin ixa	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
Bilirubin IX-alpha	HMDB
Cholerythrin	HMDB
Hematoidin	HMDB
Bilirubin IX alpha	HMDB

Molecular Formula

C₃₃H₃₆N₄O₆

Average Mass

584.6621

Monoisotopic Mass

584.263484904

IUPAC Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

Traditional Name

bilirubin

CAS Registry Number

Not Available

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

InChI Identifier

InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-

InChI Key

BPYKTIZUTYGOLE-IFADSCNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

Bilirubin skeleton
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:16990 )
biladienes (CHEBI:16990 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	3.22	ALOGPS
logP	3.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.38 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	168.9 m³·mol⁻¹	ChemAxon
Polarizability	66.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vr-0100090000-d19585e898437e8be1d5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01vn-3100069000-c39a7113e7f8eb3fa22a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Bilirubin,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-0090000000-50ff729317f07f6120b5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0090000000-83d0d13757dcbce35604	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0090000000-491b2676042d62727784	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-1090000000-1d547122826037e04cfb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-1090000000-30f7fa38dcf8706b38c6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1030090000-dea3b39afc072d2855c5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1090010000-369d79a300efec3a6c78	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0091050000-78e3736d034dec9b8fa9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0091000000-cc507e875cc295800fa0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-679d7d93f8aeb5b1c0d1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090020000-ea54f49e76225d251990	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0091000000-24657f467af3adfa1e8c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0020090000-5bcce058438671178ee4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0092030000-24054054aef5b235a850	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0030090000-b525a9b7bb66406e6afc	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ks-0000090000-ddf9acb7f968b9079764	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g0-0110290000-ae6f323e9f5e9e26199c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uml-1102910000-df5146b3612e4fb4ce5e	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-6deb1aed1a9c3839e2a9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053i-1010190000-7435a4388bade8e83d10	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9010240000-cc90fff0581c6bcefd0d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0010090000-d21be2c11a0dfd17c6e9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0030190000-749f82b203e182b3e46f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kac-0291230000-962a583eff6dd8d5cf73	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0010090000-467141ca1354a02b0aef	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C, experimental)		2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)		2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Bile
Blood
Bone Marrow
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Erythrocyte
Feces
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Thyroid Gland
Urine

Tissue Locations

Bile
Bone Marrow
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191869	Heme oxygenase 1	Unknown	P09601	Homo sapiens
MMDBp0192111	UDP-glucuronosyltransferase 2B28	Enzyme	Q9BY64	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192136	UDP-glucuronosyltransferase 2B10	Enzyme	P36537	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192138	UDP-glucuronosyltransferase 2B15	Enzyme	P54855	Homo sapiens
MMDBp0192139	UDP-glucuronosyltransferase 2A1	Enzyme	Q9Y4X1	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192142	UDP-glucuronosyltransferase 1-8	Enzyme	Q9HAW9	Homo sapiens
MMDBp0192143	UDP-glucuronosyltransferase 1-3	Enzyme	P35503	Homo sapiens
MMDBp0192144	UDP-glucuronosyltransferase 1-10	Enzyme	Q9HAW8	Homo sapiens
MMDBp0192145	UDP-glucuronosyltransferase 2B17	Enzyme	O75795	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens
MMDBp0192147	UDP-glucuronosyltransferase 1-5	Enzyme	P35504	Homo sapiens
MMDBp0192148	UDP-glucuronosyltransferase 2B11	Enzyme	O75310	Homo sapiens
MMDBp0192151	UDP-glucuronosyltransferase 1-7	Enzyme	Q9HAW7	Homo sapiens
MMDBp0192339	Biliverdin reductase A	Unknown	P53004	Homo sapiens
MMDBp0192340	Flavin reductase (NADPH)	Unknown	P30043	Homo sapiens
MMDBp0193190	Canalicular multispecific organic anion transporter 1	Transporter	Q92887	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0193408	Serum albumin	Unknown	P02768	Homo sapiens
MMDBp0193518	Alpha-fetoprotein	Unknown	P02771	Homo sapiens
MMDBp0194142	UDP-glucuronosyltransferase 2A3	Enzyme	Q6UWM9	Homo sapiens
MMDBp0195932	HCG2039726, isoform CRA_f	Enzyme	Q5DT02	Homo sapiens
MMDBp0195933	HCG2039726, isoform CRA_e	Enzyme	Q5DSZ6	Homo sapiens
MMDBp0195934	UDP glycosyltransferase 1 family polypeptide A7	Enzyme	Q5DSZ7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000392	Biliverdin	Bilirubin	biliverdin reductase A	VMH; KEGG	12456881 7656592 8117274
MMDBr0002327	Bilirubin	Mono(Glucosyluronic Acid)Bilirubin	UDP glucuronosyltransferase 1 family, polypeptide A1	VMH	7945246
MMDBr0002329	Bilirubin	Bilirubin diglucuronide	UDP glucuronosyltransferase 1 family, polypeptide A1	VMH	15117964 9295054
MMDBr0006784	Bilirubin	Mono(Glucosyluronic Acid)Bilirubin	Not Available	VMH	30371894
MMDBr0010302	Biliverdin	Bilirubin	biliverdin reductase A	VMH; KEGG	30371894
MMDBr0010303	Bilirubin diglucuronide	Mono(Glucosyluronic Acid)Bilirubin	Not Available	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cerebral vasospasm	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15789034
Crigler-najjar syndrome type i		Association	Human Blood	HMDB	6814411
Crohn's disease		Association	Human Bile	HMDB	16440420
Gallbladder disease		Association	Human Bile	HMDB	16440420
Growth hormone deficiency		Association	Human Blood	HMDB	16384844
Primary hypomagnesemia		Association	Human Blood	HMDB	10337938
Crigler-najjar syndrome type i		Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	3	Human stool; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Species	Data Source	Reference
Animal	Clupea harengus harengus	FooDB	31437929
Animal	Undaria pinnatifida	FooDB	31437929
Animal	Peprilus triacanthus	FooDB	31437929
Animal	Rhodophyta	FooDB	31437929
Animal	Myoxocephalus	FooDB	31437929
Animal	Eucheuma	FooDB	31437929
Animal	Saccharina japonica	FooDB	31437929
Animal	Spirulina	FooDB	31437929
Animal	Lota lota	FooDB	31437929
Animal	Porphyra umbilicalis	FooDB	31437929
Animal	Chondrus crispus	FooDB	31437929
Animal	Laminaria	FooDB	31437929
Animal	Haliotis	FooDB	31437929
Animal	Strombidae	FooDB	31437929
Plant	Ribes x nidigrolaria	FooDB	31437929
Plant	Ananas comosus	FooDB	31437929
Plant	Persea americana	FooDB	31437929
Plant	Garcinia mangostana	FooDB	31437929
Plant	Dioscorea pentaphylla	FooDB	31437929
Plant	Allium tuberosum	FooDB	31437929
Plant	Lathyrus sativus	FooDB	31437929
Plant	Brassica oleracea var. botrytis	FooDB	31437929
Plant	Cichorium intybus	FooDB	31437929
Plant	Corchorus olitorius	FooDB	31437929
Plant	Chenopodium quinoa	FooDB	31437929
Plant	Cucumis melo	FooDB	31437929
Plant	Juglans nigra	FooDB	31437929
Plant	Gaylussacia baccata	FooDB	31437929
Plant	Petasites japonicus	FooDB	31437929
Plant	Prunus tomentosa	FooDB	31437929
Plant	Maranta arundinacea	FooDB	31437929
Plant	Mentha x piperita	FooDB	31437929
Plant	Cinnamomum verum	FooDB	31437929
Plant	Matteuccia struthiopteris	FooDB	31437929
Plant	Cucurbita moschata	FooDB	31437929
Plant	Vaccinium myrtilloides	FooDB	31437929
Plant	Tilia	FooDB	31437929
Plant	Macadamia	FooDB	31437929
Plant	Ocimum basilicum	FooDB	31437929
Plant	Nelumbo	FooDB	31437929
Plant	Rosa	FooDB	31437929
Plant	Apium graveolens var. rapaceum	FooDB	31437929
Plant	Papaver	FooDB	31437929
Plant	Brassica oleracea var. conica	FooDB	31437929
Plant	Capsicum annuum var. annuum	FooDB	31437929
Plant	Glycine max	FooDB	31437929
Plant	Citrus limon	FooDB	31437929
Plant	Lippia graveolens	FooDB	31437929
Plant	Annona cherimola	FooDB	31437929
Plant	Brassica rapa var. pekinensis	FooDB	31437929
Plant	Brassica rapa	FooDB	31437929
Plant	Sesamum orientale	FooDB	31437929
Plant	Prunus	FooDB	31437929
Plant	Capparis spinosa	FooDB	31437929
Plant	Vaccinium deliciosum	FooDB	31437929
Plant	Citrus sinensis	FooDB	31437929
Plant	Artocarpus heterophyllus	FooDB	31437929
Plant	Prunus virginiana	FooDB	31437929
Plant	Lens culinaris	FooDB	31437929
Plant	Phaseolus lunatus	FooDB	31437929
Plant	Macadamia tetraphylla	FooDB	31437929
Plant	Musa acuminata	FooDB	31437929
Plant	Carissa macrocarpa	FooDB	31437929
Plant	Lagenaria siceraria	FooDB	31437929
Plant	Linum usitatissimum	FooDB	31437929
Plant	Citrullus lanatus	FooDB	31437929
Plant	Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant	Satureja hortensis	FooDB	31437929
Plant	Sorbus aucuparia	FooDB	31437929
Plant	Phyllostachys edulis	FooDB	31437929
Plant	Averrhoa carambola	FooDB	31437929
Plant	Carum carvi	FooDB	31437929
Plant	Allium schoenoprasum	FooDB	31437929
Plant	Citrus reticulata	FooDB	31437929
Plant	Prunus domestica	FooDB	31437929
Plant	Prunus armeniaca	FooDB	31437929
Plant	Brassica oleracea var. costata	FooDB	31437929
Plant	Panax	FooDB	31437929
Plant	Nelumbo nucifera	FooDB	31437929
Plant	Brassica rapa var. rapa	FooDB	31437929
Plant	Cymbopogon citratus	FooDB	31437929
Plant	Bertholletia excelsa	FooDB	31437929
Plant	Ceratonia siliqua	FooDB	31437929
Plant	Vigna umbellata	FooDB	31437929
Plant	Luffa aegyptiaca	FooDB	31437929
Plant	Anethum graveolens	FooDB	31437929
Plant	Coriandrum sativum	FooDB	31437929
Plant	Rubus occidentalis	FooDB	31437929
Plant	Allium fistulosum	FooDB	31437929
Plant	Capsicum	FooDB	31437929
Plant	Tilia cordata	FooDB	31437929
Plant	Carthamus tinctorius	FooDB	31437929
Plant	Lupinus	FooDB	31437929
Plant	Vaccinium alaskaense	FooDB	31437929
Plant	Cicer arietinum	FooDB	31437929
Plant	Durio zibethinus	FooDB	31437929
Plant	Anacardium occidentale	FooDB	31437929
Plant	Prunus persica var. nucipersica	FooDB	31437929
Plant	Ribes glandulosum	FooDB	31437929
Plant	Eriobotrya japonica	FooDB	31437929
Plant	Brassica napus var. pabularia	FooDB	31437929
Plant	Verbena officinalis	FooDB	31437929
Plant	Oenothera biennis	FooDB	31437929
Plant	Vaccinium oxycoccos	FooDB	31437929
Plant	Diospyros kaki	FooDB	31437929
Plant	Rumex acetosa	FooDB	31437929
Plant	Virola surinamensis	FooDB	31437929
Plant	Theobroma cacao	FooDB	31437929
Plant	Aloysia triphylla	FooDB	31437929
Plant	Vaccinium parvifolium	FooDB	31437929
Plant	Camellia sinensis	FooDB	31437929
Plant	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Capsicum chinense	FooDB	31437929
Plant	Brassica oleracea var. capitata	FooDB	31437929
Plant	Pyrus pyrifolia	FooDB	31437929
Plant	Vaccinium reticulatum	FooDB	31437929
Plant	Solanum quitoense	FooDB	31437929
Plant	Vaccinium myrtillus	FooDB	31437929
Plant	Theobroma grandiflorum	FooDB	31437929
Plant	Phaseolus vulgaris	FooDB	31437929
Plant	Syzygium aromaticum	FooDB	31437929
Plant	Daucus carota ssp. sativus	FooDB	31437929
Plant	Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant	Ginkgo biloba	FooDB	31437929
Plant	Satureja montana	FooDB	31437929
Plant	Perideridia oregana	FooDB	31437929
Plant		FooDB	31437929
Plant	Flammulina velutipes	FooDB	31437929
Plant	Vaccinium arboreum	FooDB	31437929
Plant	Citrus japonica	FooDB	31437929
Plant	Wasabia japonica	FooDB	31437929
Plant	Origanum onites	FooDB	31437929
Plant	Vicia faba	FooDB	31437929
Plant	Pouteria sapota	FooDB	31437929
Plant	Prunus avium	FooDB	31437929
Plant	Viburnum edule	FooDB	31437929
Plant	Piper nigrum	FooDB	31437929
Plant	Vitis vinifera	FooDB	31437929
Plant	Vaccinium uliginosum	FooDB	31437929
Plant	Dioscorea	FooDB	31437929
Plant	Origanum vulgare	FooDB	31437929
Plant	Capsicum annuum	FooDB	31437929
Plant	Momordica charantia	FooDB	31437929
Plant	Castanea	FooDB	31437929
Plant	Rubus ursinus x idaeus	FooDB	31437929
Plant	Cirsium	FooDB	31437929
Plant	Raphanus sativus var. sativus	FooDB	31437929
Plant	Opuntia	FooDB	31437929
Plant	Prunus persica var. persica	FooDB	31437929
Plant	Pleurotus ostreatus	FooDB	31437929
Plant	Colocasia esculenta	FooDB	31437929
Plant	Brassica oleracea var. italica	FooDB	31437929
Plant	Anthriscus cerefolium	FooDB	31437929
Plant	Solanum melongena	FooDB	31437929
Plant	Nuphar lutea	FooDB	31437929
Plant	Pachyrhizus erosus	FooDB	31437929
Plant	Lupinus albus	FooDB	31437929
Plant	Dysphania ambrosioides	FooDB	31437929
Plant	Cichorium endivia	FooDB	31437929
Plant	Raphanus sativus var. niger	FooDB	31437929
Plant	Myristica fragrans	FooDB	31437929
Plant	Elaeis	FooDB	31437929
Plant	Cinnamomum	FooDB	31437929
Plant	Photinia melanocarpa	FooDB	31437929
Plant	Ribes uva-crispa	FooDB	31437929
Plant	Feijoa sellowiana	FooDB	31437929
Plant	Vaccinium	FooDB	31437929
Plant	Apium graveolens	FooDB	31437929
Plant	Syzygium jambos	FooDB	31437929
Plant	Rheum rhabarbarum	FooDB	31437929
Plant	Crocus sativus	FooDB	31437929
Plant	Salix pulchra	FooDB	31437929
Plant	Lablab purpureus	FooDB	31437929
Plant	Fagus	FooDB	31437929
Plant	Citrus maxima	FooDB	31437929
Plant	Cydonia oblonga	FooDB	31437929
Plant	Castanea sativa	FooDB	31437929
Plant	Salvia officinalis	FooDB	31437929
Plant	Vaccinium ovatum	FooDB	31437929
Plant	Opuntia cochenillifera	FooDB	31437929
Plant	Annona muricata	FooDB	31437929
Plant	Thymus pulegioides	FooDB	31437929
Plant	Mespilus germanica	FooDB	31437929
Plant	Cucurbita	FooDB	31437929
Plant	Phaseolus coccineus	FooDB	31437929
Plant	Brassica rapa var. perviridis	FooDB	31437929
Plant	Cocos nucifera	FooDB	31437929
Plant	Tamarindus indica	FooDB	31437929
Plant	Mentha aquatica	FooDB	31437929
Plant	Salvia elegans	FooDB	31437929
Plant	Mentha	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Sagittaria latifolia	FooDB	31437929
Plant	Sambucus	FooDB	31437929
Plant	Syzygium cumini	FooDB	31437929
Plant	Typha angustifolia	FooDB	31437929
Plant	Psidium guajava	FooDB	31437929
Plant	Empetrum nigrum	FooDB	31437929
Plant	Myrica rubra	FooDB	31437929
Plant	Pinus	FooDB	31437929
Plant	Tilia tomentosa	FooDB	31437929
Plant	Olea europaea	FooDB	31437929
Plant	Valerianella locusta	FooDB	31437929
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant	Sisymbrium	FooDB	31437929
Plant	Vaccinium vitis-idaea	FooDB	31437929
Plant	Vanilla	FooDB	31437929
Plant	Daucus carota	FooDB	31437929
Plant	Solanum tuberosum	FooDB	31437929
Plant	Carya	FooDB	31437929
Plant	Physalis philadelphica var. immaculata	FooDB	31437929
Plant	Borago officinalis	FooDB	31437929
Plant	Scorzonera hispanica	FooDB	31437929
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Hyssopus officinalis	FooDB	31437929
Plant	Manihot esculenta	FooDB	31437929
Plant	Angelica keiskei	FooDB	31437929
Plant	Raphanus sativus	FooDB	31437929
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Ipomoea aquatica	FooDB	31437929
Plant	Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Prunus dulcis	FooDB	31437929
Plant	Rubus spectabilis	FooDB	31437929
Plant	Vigna radiata	FooDB	31437929
Plant	Musa x paradisiaca	FooDB	31437929
Plant	Allium sativum	FooDB	31437929
Plant	Cantharellus cibarius	FooDB	31437929
Plant	Cuminum cyminum	FooDB	31437929
Plant	Sinapis alba	FooDB	31437929
Plant	Brassica ruvo	FooDB	31437929
Plant	Fragaria x ananassa	FooDB	31437929
Plant	Pyrus communis	FooDB	31437929
Plant	Morus nigra	FooDB	31437929
Plant	Apium graveolens var. secalinum	FooDB	31437929
Plant	Rubus idaeus	FooDB	31437929
Plant	Arachis hypogaea	FooDB	31437929
Plant	Pinus edulis	FooDB	31437929
Plant	Abelmoschus esculentus	FooDB	31437929
Plant	Opuntia macrorhiza	FooDB	31437929
Plant	Solanum lycopersicum	FooDB	31437929
Plant	Moringa oleifera	FooDB	31437929
Plant	Passiflora edulis	FooDB	31437929
Plant	Manilkara zapota	FooDB	31437929
Plant	Vigna angularis	FooDB	31437929
Plant	Allium cepa	FooDB	31437929
Plant	Malus	FooDB	31437929
Plant	Mentha spicata	FooDB	31437929
Plant	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Corylus	FooDB	31437929
Plant	Juglans	FooDB	31437929
Plant	Sambucus nigra	FooDB	31437929
Plant		FooDB	31437929
Plant	Mangifera indica	FooDB	31437929
Plant	Illicium verum	FooDB	31437929
Plant	Helianthus annuus	FooDB	31437929
Plant	Ribes nigrum	FooDB	31437929
Plant	Chamaemelum nobile	FooDB	31437929
Plant	Auricularia auricula-judae	FooDB	31437929
Plant	Zingiber officinale	FooDB	31437929
Plant	Laurus nobilis	FooDB	31437929
Plant	Petroselinum crispum	FooDB	31437929
Plant	Juglans ailanthifolia	FooDB	31437929
Plant	Attalea speciosa	FooDB	31437929
Plant	Polygonum alpinum	FooDB	31437929
Plant	Pisum sativum	FooDB	31437929
Plant	Hippophae rhamnoides	FooDB	31437929
Plant	Melissa officinalis	FooDB	31437929
Plant	Pediomelum esculentum	FooDB	31437929
Plant	Auricularia polytricha	FooDB	31437929
Plant	Brassica juncea	FooDB	31437929
Plant	Vaccinium corymbosum	FooDB	31437929
Plant	Camellia oleifera	FooDB	31437929
Plant	Chrysanthemum coronarium	FooDB	31437929
Plant	Eleocharis dulcis	FooDB	31437929
Plant	Actinidia chinensis	FooDB	31437929
Plant	Rubus arcticus	FooDB	31437929
Plant	Spinacia oleracea	FooDB	31437929
Plant	Carica papaya	FooDB	31437929
Plant	Thymus vulgaris	FooDB	31437929
Plant	Pimenta dioica	FooDB	31437929
Plant	Rumex articus	FooDB	31437929
Plant	Medicago sativa	FooDB	31437929
Plant	Hibiscus sabdariffa	FooDB	31437929
Plant	Agaricus bisporus	FooDB	31437929
Plant	Canarium ovatum	FooDB	31437929
Plant	Ribes aureum var. villosum	FooDB	31437929
Plant	Vigna mungo	FooDB	31437929
Plant	Benincasa hispida	FooDB	31437929
Plant	Cajanus cajan	FooDB	31437929
Plant	Armoracia rusticana	FooDB	31437929
Plant	Origanum majorana	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Prunus persica	FooDB	31437929
Plant	Eruca vesicaria ssp. sativa	FooDB	31437929
Plant	Juglans cinerea	FooDB	31437929
Plant	Vaccinium macrocarpon	FooDB	31437929
Plant	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Foeniculum vulgare	FooDB	31437929
Plant	Arctium lappa	FooDB	31437929
Plant	Phoenix dactylifera	FooDB	31437929
Plant	Metroxylon sagu	FooDB	31437929
Plant	Artocarpus altilis	FooDB	31437929
Plant	Vitis rotundifolia	FooDB	31437929
Plant	Psidium cattleianum	FooDB	31437929
Plant	Cyathea	FooDB	31437929
Plant	Vigna unguiculata	FooDB	31437929
Plant	Brosimum alicastrum	FooDB	31437929
Plant	Cynara scolymus	FooDB	31437929
Plant	Castanea mollissima	FooDB	31437929
Plant	Rosmarinus officinalis	FooDB	31437929
Plant	Lentinus edodes	FooDB	31437929
Plant		FooDB	31437929
Plant	Prunus cerasus	FooDB	31437929
Plant	Citrus x paradisi	FooDB	31437929
Plant	Morus	FooDB	31437929
Plant	Ficus carica	FooDB	31437929
Plant	Vitis labrusca	FooDB	31437929
Plant	Lepidium sativum	FooDB	31437929
Plant	Phytolacca americana	FooDB	31437929
Plant	Helianthus tuberosus	FooDB	31437929
Plant	Cucumis metuliferus	FooDB	31437929
Plant	Myrica	FooDB	31437929
Plant	Grifola frondosa	FooDB	31437929
Plant	Beta vulgaris var. rubra	FooDB	31437929
Plant	Nephelium lappaceum	FooDB	31437929
Plant	Tetragonia tetragonioides	FooDB	31437929
Plant	Artemisia vulgaris	FooDB	31437929
Plant	Castanea crenata	FooDB	31437929
Plant	Quercus	FooDB	31437929
Plant	Corylus avellana	FooDB	31437929
Plant	Vaccinium angustifolium	FooDB	31437929
Plant	Litchi chinensis	FooDB	31437929
Plant	Physalis	FooDB	31437929
Plant	Malpighia emarginata	FooDB	31437929
Plant	Thelesperma	FooDB	31437929
Plant	Juglans regia	FooDB	31437929
Plant	Trigonella foenum-graecum	FooDB	31437929
Plant	Chamerion angustifolium	FooDB	31437929
Plant	Brassica oleracea var. sabauda	FooDB	31437929
Plant	Vaccinium elliottii	FooDB	31437929
Plant	Brassica napus	FooDB	31437929
Plant		FooDB	31437929
Plant	Levisticum officinale	FooDB	31437929
Plant	Asparagus officinalis	FooDB	31437929
Plant	Ziziphus zizyphus	FooDB	31437929
Plant	Dimocarpus longan	FooDB	31437929
Plant	Salvia hispanica	FooDB	31437929
Plant	Citrus aurantiifolia	FooDB	31437929
Plant	Cynara cardunculus	FooDB	31437929
Plant	Pangium edule	FooDB	31437929
Plant	Matricaria recutita	FooDB	31437929
Plant	Lactuca sativa	FooDB	31437929
Plant	Pimpinella anisum	FooDB	31437929
Plant	Allium	FooDB	31437929
Plant	Artemisia dracunculus	FooDB	31437929
Plant	Brassica oleracea var. viridis	FooDB	31437929
Plant	Agave	FooDB	31437929
Plant	Hedysarum alpinum	FooDB	31437929
Plant	Vitellaria paradoxa	FooDB	31437929
Plant	Eragrostis tef	FooDB	31437929
Plant	Vigna aconitifolia	FooDB	31437929
Plant	Pistacia vera	FooDB	31437929
Plant	Diospyros	FooDB	31437929
Plant	Amaranthus	FooDB	31437929
Plant	Mammea americana	FooDB	31437929
Plant	Punica granatum	FooDB	31437929
Plant	Malus pumila	FooDB	31437929
Plant	Annona squamosa	FooDB	31437929
Plant	Gossypium	FooDB	31437929
Plant	Brassica alboglabra	FooDB	31437929
Plant	Apium graveolens var. dulce	FooDB	31437929
Plant	Beta vulgaris	FooDB	31437929
Plant	Xanthosoma sagittifolium	FooDB	31437929
Plant	Basella alba	FooDB	31437929
Plant	Capsicum baccatum var. baccatum	FooDB	31437929
Plant	Vitis	FooDB	31437929
Plant	Citrus latifolia	FooDB	31437929
Plant	Byrsonima crassifolia	FooDB	31437929
Plant	Capsicum pubescens	FooDB	31437929
Plant		FooDB	31437929
Plant	Carya illinoinensis	FooDB	31437929
Plant	Crateva religiosa	FooDB	31437929
Plant	Vitis aestivalis	FooDB	31437929
Plant	Eugenia javanica	FooDB	31437929
Plant	Mentha arvensis	FooDB	31437929
Plant	Cucumis sativus	FooDB	31437929
Plant	Vaccinium stamineum	FooDB	31437929
Plant		FooDB	31437929
Plant	Brassica rapa var. chinensis	FooDB	31437929
Plant	Cinnamomum aromaticum	FooDB	31437929
Plant	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Ribes rubrum	FooDB	31437929
Plant	Portulaca oleracea	FooDB	31437929
Plant	Ipomoea batatas	FooDB	31437929
Plant	Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant	Allium ampeloprasum	FooDB	31437929
Plant	Chenopodium album	FooDB	31437929
Plant	Grataegosorbus mitschurinii	FooDB	31437929
Plant	Pastinaca sativa	FooDB	31437929
Plant	Cucurbita maxima	FooDB	31437929
Plant	Sechium edule	FooDB	31437929
Plant	Brassica oleracea	FooDB	31437929
Plant	Diospyros virginiana	FooDB	31437929
Plant	Origanum x majoricum	FooDB	31437929
Plant	Rumex	FooDB	31437929
Plant	Lactuca sativa l. var. longifolia	FooDB	31437929
Plant	Rubus x loganobaccus	FooDB	31437929
Plant	Tragopogon porrifolius	FooDB	31437929
Plant	Allium ascalonicum	FooDB	31437929
Plant	Citrullus lanatus var. fistulosus	FooDB	31437929
Plant	Rubus chamaemorus	FooDB	31437929
Plant	Amelanchier alnifolia	FooDB	31437929
Plant	Eugenia uniflora	FooDB	31437929
Plant	Taraxacum officinale	FooDB	31437929
Plant	Annona reticulata	FooDB	31437929
Plant	Curcuma longa	FooDB	31437929
Plant	Sesbania bispinosa	FooDB	31437929
Plant	Elettaria cardamomum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified			25.656	78.678	uM	Adult (>18 years old)	Both	Anemia, congenital dyserythropoietic, type II	HMDB	19621418
Human Blood	Detected and Quantified	106				uM	Infant (0-1 year old)	Female	Bile Acid Synthesis Defect, Congenital, 1	HMDB	26712441
Human Cerebrospinal fluid (csf)	Detected and Quantified	17.3	12.4			uM	Adult (>18 years old)	Both	Cerebral Vasospasm	HMDB	15789034
Human Blood	Detected and Quantified			18.814	518.248	uM	Adult (>18 years old)	Male	Cholestasis, progressive familial intrahepatic, 1	HMDB	15448432
Human Blood	Detected and Quantified	41		6	381	uM	Children (1-13 years old)	Both	Cholestasis, progressive familial intrahepatic, 1	HMDB	22424345
Human Blood	Detected and Quantified			42.760	141.962	uM	Children (1-13 years old)	Female	Cholestasis, progressive familial intrahepatic, 1	HMDB	15448432
Human Blood	Detected and Quantified			22	41	uM	Newborn (0-30 days old)	Both	Citrullinemia type II, neonatal-onset	HMDB	11281457
Human Blood	Detected and Quantified			41	101	uM	Newborn (0-30 days old)	Both	Citrullinemia type II, neonatal-onset	HMDB	11281457
Human Blood	Detected and Quantified	650				uM	Adolescent (13-18 years old)	Male	Crigler-Najjar syndrome Type I	HMDB	6814411
Human Bile	Detected and Quantified	4600		3900	5300	uM	Adult (>18 years old)	Both	Crohn's disease	HMDB	16440420
Human Bile	Detected and Quantified	5000		4300	5700	uM	Adult (>18 years old)	Both	Crohn's disease	HMDB	16440420
Human Bile	Detected and Quantified	5900		4300	7500	uM	Adult (>18 years old)	Both	Crohn's disease	HMDB	16440420
Human Blood	Detected and Quantified	78.678				uM	Newborn (0-30 days old)	Male	Donohue Syndrome	HMDB	26871809
Human Blood	Detected and Quantified	111.175				uM	Newborn (0-30 days old)	Male	Donohue Syndrome	HMDB	26871809
Human Bile	Detected and Quantified	2600		2400	2800	uM	Adult (>18 years old)	Both	Gallstone disease	HMDB	16440420
Human Blood	Detected and Quantified	380.733	142.989			uM	Newborn (0-30 days old)	Both	Glucose-6-phosphate dehydrogenase deficiency	HMDB	14703221
Human Blood	Detected and Quantified	14.6	2.5			uM	Adult (>18 years old)	Both	Growth hormone deficiency	HMDB	16384844
Human Blood	Detected and Quantified	8.80	1.22			uM	Adult (>18 years old)	Both	Growth hormone deficiency	HMDB	16384844
Human Blood	Detected and Quantified			28.7	170	uM	Children (1-13 years old)	Both	Infantile Liver Failure Syndrome 2	HMDB	26541327
Human Blood	Detected and Quantified			46.9	233	uM	Children (1-13 years old)	Both	Infantile Liver Failure Syndrome 2	HMDB	26541327
Human Blood	Detected and Quantified			73.1	85.0	uM	Infant (0-1 year old)	Female	Infantile Liver Failure Syndrome 2	HMDB	26541327
Human Blood	Detected and Quantified	29.59				uM	Newborn (0-30 days old)	Male	Lathosterolosis	HMDB	12189593
Human Blood	Detected and Quantified	42.247				uM	Newborn (0-30 days old)	Male	Lathosterolosis	HMDB	12189593
Human Blood	Detected and Quantified	24.5				uM	Adult (>18 years old)	Female	Lecithin:cholesterol Acyltransferase Deficiency	HMDB	16051254
Human Blood	Detected and Quantified			6.842	20.525	uM	Adult (>18 years old)	Male	Primary Hypomagnesemia	HMDB	10337938
Human Blood	Detected and Quantified			3	21	uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	11281457
Human Blood	Detected and Quantified	<12				uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	11281457
Human Blood	Detected and Quantified	<12.828				uM	Adult (>18 years old)	Both	Normal	HMDB	19621418
Human Blood	Detected and Quantified	<20				uM	Children (1-13 years old)	Not Specified	Normal	HMDB	26541327
Human Blood	Detected and Quantified	<3.4				uM	Children (1-13 years old)	Not Specified	Normal	HMDB	26541327
Human Blood	Detected and Quantified	15.2	2.0			uM	Adult (>18 years old)	Both	Normal	HMDB	16384844
Human Blood	Detected and Quantified	310.265	65.850			uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	14703221
Human Blood	Detected and Quantified			6.842	20.525	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	15448432
Human Blood	Detected and Quantified	8.0	0.9			uM	Adult (>18 years old)	Both	Normal	HMDB	16384844
Human Blood	Detected and Quantified	573.0		291.0	855.0	uM	Children (1-13 years old)	Both	Crigler-Najjar syndrome Type I	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	59.2				uM	Infant (0-1 year old)	Female	Wolcott-Rallison syndrome	HMDB	Neonatal diabetes in Wolcott-Rallison syndrome: a case report
Human Urine	Detected and Quantified			0.51	5.13	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	0.2	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.032		0.0019	0.21	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	8.500	4			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	<17				uM	Children (1 - 13 years old)		Normal	HMDB	Hereditary Jaundice and Disorders of Bilirubin Metabolism. In: Valle D, Beaudet AL, Vogelstein B, Kinzler KW, Antonarakis SE, Ballabio A, Gibson K, Mitchell G. eds. The Online Metabolic and Molecular Bases of Inherited Disease New York, NY. http://ommbid.mhmedical.com.login.ezproxy.library.ualberta.ca/content.aspx?bookid=971&sectionid=62639411
Human Blood	Detected and Quantified	13.0		5.0	21.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Louise M. Malarkey, Mary Ellen McMorrow. Saunders Nursing Guide to Diagnostic and Laboratory Tests. Elsevier Health Sciences, Nov 1, 2011.
Human Urine	Detected and Quantified	< 0.1				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Tietz Clinical Guide to Laboratory Tests 4th Ed., 2006.
Human Blood	Detected and Quantified			5.10	18.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Blood	Detected and Quantified			5.131	17.104	uM	Adult (>18 years old)	Both	Normal	HMDB	Vancouver Coastal Health Lab (http://www.vch.ca/Locations-Services/result?res_id=601)
Human Bile	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Bone marrow	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24740205
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

5280352

PDB ID

Not Available

ChEBI ID

16990

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bayes Garcia R, Maldonado Lozano J, Molina Font JA: [Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions]. An Esp Pediatr. 1989 Jan;30(1):27-31. [PubMed:2648917 ]
Tiribelli C, Ostrow JD: New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. Hepatology. 1996 Nov;24(5):1296-311. doi: 10.1002/hep.510240551. [PubMed:8903413 ]
Kotal P, Van der Veere CN, Sinaasappel M, Elferink RO, Vitek L, Brodanova M, Jansen PL, Fevery J: Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. Pediatr Res. 1997 Aug;42(2):195-200. doi: 10.1203/00006450-199708000-00011. [PubMed:9262222 ]
Kikuchi S, Hata M, Fukumoto K, Yamane Y, Matsui T, Tamura A, Yonemura S, Yamagishi H, Keppler D, Tsukita S, Tsukita S: Radixin deficiency causes conjugated hyperbilirubinemia with loss of Mrp2 from bile canalicular membranes. Nat Genet. 2002 Jul;31(3):320-5. doi: 10.1038/ng905. Epub 2002 Jun 17. [PubMed:12068294 ]
Lin JM, Jiang CQ: [Clinical manifestation and ultrasonic characteristics of five patients with acute arsenic poisoning]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2003 Dec;21(6):420-2. [PubMed:14761351 ]
Sikkel E, Pasman SA, Oepkes D, Kanhai HH, Vandenbussche FP: On the origin of amniotic fluid bilirubin. Placenta. 2004 May;25(5):463-8. doi: 10.1016/j.placenta.2003.10.015. [PubMed:15081641 ]
Slusher TM, Angyo IA, Bode-Thomas F, Akor F, Pam SD, Adetunji AA, McLaren DW, Wong RJ, Vreman HJ, Stevenson DK: Transcutaneous bilirubin measurements and serum total bilirubin levels in indigenous African infants. Pediatrics. 2004 Jun;113(6):1636-41. doi: 10.1542/peds.113.6.1636. [PubMed:15173484 ]
Zhan X, Wang SY, Wang L, Qu P: [Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome]. Zhonghua Er Ke Za Zhi. 2004 May;42(5):362-6. [PubMed:15189696 ]
Kabicek P: Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia. Cent Eur J Public Health. 2004 Jun;12(2):102-9. [PubMed:15242029 ]
Yamamoto S, Kubo S, Hai S, Uenishi T, Yamamoto T, Shuto T, Takemura S, Tanaka H, Yamazaki O, Hirohashi K, Tanaka T: Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma. Cancer Sci. 2004 Jul;95(7):592-5. doi: 10.1111/j.1349-7006.2004.tb02492.x. [PubMed:15245596 ]
Schmidt CM, Powell ES, Yiannoutsos CT, Howard TJ, Wiebke EA, Wiesenauer CA, Baumgardner JA, Cummings OW, Jacobson LE, Broadie TA, Canal DF, Goulet RJ Jr, Curie EA, Cardenes H, Watkins JM, Loehrer PJ, Lillemoe KD, Madura JA: Pancreaticoduodenectomy: a 20-year experience in 516 patients. Arch Surg. 2004 Jul;139(7):718-25; discussion 725-7. doi: 10.1001/archsurg.139.7.718. [PubMed:15249403 ]
Danko I, Jia Z, Zhang G: Nonviral gene transfer into liver and muscle for treatment of hyperbilirubinemia in the gunn rat. Hum Gene Ther. 2004 Dec;15(12):1279-86. doi: 10.1089/hum.2004.15.1279. [PubMed:15684703 ]
Azer SA: A multimedia CD-ROM tool to improve student understanding of bile salts and bilirubin metabolism: evaluation of its use in a medical hybrid PBL course. Adv Physiol Educ. 2005 Mar;29(1):40-50. doi: 10.1152/advan.00015.2004. [PubMed:15718382 ]
Nanjundaswamy S, Petrova A, Mehta R, Hegyi T: Transcutaneous bilirubinometry in preterm infants receiving phototherapy. Am J Perinatol. 2005 Apr;22(3):127-31. doi: 10.1055/s-2005-863785. [PubMed:15838745 ]
Randeberg LL, Roll EB, Nilsen LT, Christensen T, Svaasand LO: In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index. Acta Paediatr. 2005 Jan;94(1):65-71. doi: 10.1111/j.1651-2227.2005.tb01790.x. [PubMed:15858963 ]
Deja M, Hildebrandt B, Ahlers O, Riess H, Wust P, Gerlach H, Kerner T: Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. Chest. 2005 Aug;128(2):580-6. doi: 10.1378/chest.128.2.580. [PubMed:16100141 ]
Sando M, Sato Y, Iwata S, Akita H, Sunakawa K: In vitro protein binding of teicoplanin to neonatal serum. J Infect Chemother. 2004 Oct;10(5):280-3. doi: 10.1007/s10156-004-0339-x. [PubMed:16163462 ]
Ciszowski K, Gomolka E, Jenner B: [The influence of the dose, time since ingestion and concentration of the xenobiotic on the clinical state and severity of liver damage with patients intoxicated with paracetamol]. Przegl Lek. 2005;62(6):456-61. [PubMed:16225094 ]
Lapidus A, Akerlund JE, Einarsson C: Gallbladder bile composition in patients with Crohn 's disease. World J Gastroenterol. 2006 Jan 7;12(1):70-4. doi: 10.3748/wjg.v12.i1.70. [PubMed:16440420 ]
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Showing metabocard for Bilirubin (MMDBc0000328)

MOL for #<Metabolite:0x00007f46d8f8ff68>

3D MOL for #<Metabolite:0x00007f46d8f8ff68>

3D SDF for #<Metabolite:0x00007f46d8f8ff68>

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PDB for #<Metabolite:0x00007f46d8f8ff68>

3D PDB for #<Metabolite:0x00007f46d8f8ff68>

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Structure for #<Metabolite:0x00007f46d8f8ff68>

3D Structure for #<Metabolite:0x00007f46d8f8ff68>