MiMeDB: Showing metabocard for D-Urobilin (MMDBc0000430)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:35 UTC

Update Date

2024-04-30 19:32:23 UTC

Metabolite ID

MMDBc0000430

Metabolite Identification

Common Name

D-Urobilin

Description

Urobilin is one of the final by-products of hemoglobin breakdown. Urobilin is excreted in both the urine and feces from many mammals, particularly humans. It is primarily responsible for the yellow color of urine. The breakdown of hemoglobin to biliverdin is common to most animals, while the next step, the conversion of biliverdin to bilirubin, and subsequently to the urobilinogens (urobilin is one particular oxidized chemical form of urobilinogen) is unique to mammals. (PMID: 16604237 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219532D          

 43 46  0  0  0  0            999 V2000
   23.4113  -23.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8873  -18.3855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6968  -22.1724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0433  -19.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2718  -19.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6741  -26.8628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1971  -20.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6345  -25.8232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1760  -22.4974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2476  -23.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9823  -23.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7379  -19.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3246  -25.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9683  -22.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2678  -22.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7239  -22.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0735  -20.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1478  -22.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7699  -26.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0708  -21.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0802  -24.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2786  -20.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1109  -21.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8095  -25.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6968  -22.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2228  -19.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2220  -27.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6282  -22.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9365  -28.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4434  -20.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8894  -26.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6601  -24.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7997  -23.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038  -21.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5546  -26.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8913  -21.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4671  -24.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5533  -23.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2220  -27.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5086  -22.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8435  -22.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7635  -21.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5886  -21.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 25  2  0  0  0  0
  4 26  2  0  0  0  0
  5 30  2  0  0  0  0
  6 31  2  0  0  0  0
  7 23  1  0  0  0  0
  7 30  1  0  0  0  0
  8 24  1  0  0  0  0
  8 31  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 32  2  0  0  0  0
 10 33  1  0  0  0  0
 11 15  1  0  0  0  0
 11 25  1  0  0  0  0
 12 17  1  0  0  0  0
 12 26  1  0  0  0  0
 13 24  1  0  0  0  0
 13 32  1  0  0  0  0
 14 18  1  0  0  0  0
 14 34  1  0  0  0  0
 15 38  1  0  0  0  0
 16 23  1  0  0  0  0
 16 40  1  0  0  0  0
 17 43  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 22 42  1  0  0  0  0
 23 34  1  0  0  0  0
 24 35  1  0  0  0  0
 27 29  2  0  0  0  0
 27 39  1  0  0  0  0
 28 33  2  0  0  0  0
 28 41  1  0  0  0  0
 30 36  1  0  0  0  0
 31 39  1  0  0  0  0
 32 37  1  0  0  0  0
 33 38  1  0  0  0  0
 34 36  2  0  0  0  0
 35 39  2  0  0  0  0
 37 38  2  0  0  0  0
 40 42  2  0  0  0  0
 41 43  2  0  0  0  0
 42 43  1  0  0  0  0
M  END


  Mrv0541 02231219532D          

 43 46  0  0  0  0            999 V2000
   23.4113  -23.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8873  -18.3855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6968  -22.1724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0433  -19.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2718  -19.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6741  -26.8628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1971  -20.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6345  -25.8232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1760  -22.4974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2476  -23.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9823  -23.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7379  -19.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3246  -25.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9683  -22.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2678  -22.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7239  -22.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0735  -20.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1478  -22.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7699  -26.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0708  -21.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0802  -24.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2786  -20.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1109  -21.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8095  -25.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6968  -22.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2228  -19.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2220  -27.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6282  -22.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9365  -28.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4434  -20.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8894  -26.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6601  -24.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7997  -23.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038  -21.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5546  -26.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8913  -21.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4671  -24.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5533  -23.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2220  -27.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5086  -22.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8435  -22.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7635  -21.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5886  -21.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 25  2  0  0  0  0
  4 26  2  0  0  0  0
  5 30  2  0  0  0  0
  6 31  2  0  0  0  0
  7 23  1  0  0  0  0
  7 30  1  0  0  0  0
  8 24  1  0  0  0  0
  8 31  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 32  2  0  0  0  0
 10 33  1  0  0  0  0
 11 15  1  0  0  0  0
 11 25  1  0  0  0  0
 12 17  1  0  0  0  0
 12 26  1  0  0  0  0
 13 24  1  0  0  0  0
 13 32  1  0  0  0  0
 14 18  1  0  0  0  0
 14 34  1  0  0  0  0
 15 38  1  0  0  0  0
 16 23  1  0  0  0  0
 16 40  1  0  0  0  0
 17 43  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 22 42  1  0  0  0  0
 23 34  1  0  0  0  0
 24 35  1  0  0  0  0
 27 29  2  0  0  0  0
 27 39  1  0  0  0  0
 28 33  2  0  0  0  0
 28 41  1  0  0  0  0
 30 36  1  0  0  0  0
 31 39  1  0  0  0  0
 32 37  1  0  0  0  0
 33 38  1  0  0  0  0
 34 36  2  0  0  0  0
 35 39  2  0  0  0  0
 37 38  2  0  0  0  0
 40 42  2  0  0  0  0
 41 43  2  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000430

> <DATABASE_NAME>
MIME

> <SMILES>
CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(CC2NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H40N4O6/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/h8,15,26-27,35H,2,7,9-14H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-

> <INCHI_KEY>
DOKCNDVEPDZOJQ-MBTHVWNTSA-N

> <FORMULA>
C33H40N4O6

> <MOLECULAR_WEIGHT>
588.6939

> <EXACT_MASS>
588.294785032

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
66.05419782164756

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
0.9379256437552342

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.475449265568898

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.884201688158971

> <JCHEM_PKA_STRONGEST_BASIC>
5.964724514983541

> <JCHEM_POLAR_SURFACE_AREA>
160.95

> <JCHEM_REFRACTIVITY>
166.30389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.96e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      43.701 -43.699   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.256 -34.320   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      42.367 -41.388   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      37.414 -35.888   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      28.507 -36.871   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      40.458 -50.144   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      30.235 -39.004   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      38.518 -48.203   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      33.929 -41.995   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      35.929 -44.217   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      41.034 -43.699   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.977 -36.973   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.073 -46.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.941 -42.262   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.700 -42.929   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.218 -41.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.604 -38.379   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.409 -42.424   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.037 -50.144   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.265 -39.361   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.350 -46.261   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.253 -38.379   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.074 -40.535   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.978 -48.203   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.367 -42.929   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      35.883 -35.727   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      37.748 -52.113   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      36.639 -41.566   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      39.081 -52.883   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.828 -38.377   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.994 -49.668   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.699 -45.551   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      36.959 -43.072   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      28.567 -40.856   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      36.502 -49.668   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      27.797 -39.522   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      38.205 -45.230   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      38.366 -43.699   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      37.748 -50.573   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      32.683 -41.090   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      35.175 -41.090   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      33.159 -39.625   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      34.699 -39.625   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   23   30                                                       
CONECT    8   24   31                                                       
CONECT    9   40   41                                                       
CONECT   10   32   33                                                       
CONECT   11   15   25                                                       
CONECT   12   17   26                                                       
CONECT   13   24   32                                                       
CONECT   14   18   34                                                       
CONECT   15   11   38                                                       
CONECT   16   23   40                                                       
CONECT   17   12   43                                                       
CONECT   18   14                                                            
CONECT   19   35                                                            
CONECT   20   36                                                            
CONECT   21   37                                                            
CONECT   22   42                                                            
CONECT   23    7   16   34                                                  
CONECT   24    8   13   35                                                  
CONECT   25    1    3   11                                                  
CONECT   26    2    4   12                                                  
CONECT   27   29   39                                                       
CONECT   28   33   41                                                       
CONECT   29   27                                                            
CONECT   30    5    7   36                                                  
CONECT   31    6    8   39                                                  
CONECT   32   10   13   37                                                  
CONECT   33   10   28   38                                                  
CONECT   34   14   23   36                                                  
CONECT   35   19   24   39                                                  
CONECT   36   20   30   34                                                  
CONECT   37   21   32   38                                                  
CONECT   38   15   33   37                                                  
CONECT   39   27   31   35                                                  
CONECT   40    9   16   42                                                  
CONECT   41    9   28   43                                                  
CONECT   42   22   40   43                                                  
CONECT   43   17   41   42                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

Synonyms

Value	Source
Urobilin	HMDB
3-[(2Z)-2-{[3-(2-carboxyethyl)-5-[(3-ethyl-5-hydroxy-4-methyl-2H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene}-5-[(4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-yl)methyl]-4-methyl-2H-pyrrol-3-yl]propanoate	Generator

Molecular Formula

C₃₃H₄₀N₄O₆

Average Mass

588.6939

Monoisotopic Mass

588.294785032

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(CC2NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O

InChI Identifier

InChI=1S/C33H40N4O6/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/h8,15,26-27,35H,2,7,9-14H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-

InChI Key

DOKCNDVEPDZOJQ-MBTHVWNTSA-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
Dipyrrin
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Imine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	2.88	ALOGPS
logP	0.94	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	5.96	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	160.95 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	166.3 m³·mol⁻¹	ChemAxon
Polarizability	66.05 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	splash10-00di-3400290000-297c3668e2c0d1785f54	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4400039000-97cf9b2d25461b5a17b8	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fki-0000090000-6e2980147c1f061ef0bb	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00bc-0210390000-775b90138889c7a18e37	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-2460960000-9e0b489f963706f156d7	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-86905dd0f735ea194700	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-1100290000-5575fb22e3d51616a089	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000330000-6c2858081f4ee4164833	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	6	Human feces; Human ; Human stool; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human vaginal fluid; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified			3.36	15.13	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004161

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023326

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Urobilin

METLIN ID

Not Available

PubChem Compound

6276321

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jones-Lepp TL: Chemical markers of human waste contamination: analysis of urobilin and pharmaceuticals in source waters. J Environ Monit. 2006 Apr;8(4):472-8. doi: 10.1039/b512858g. Epub 2006 Mar 10. [PubMed:16604237 ]

Showing metabocard for D-Urobilin (MMDBc0000430)

MOL for #<Metabolite:0x00007fdb7097cc48>

3D MOL for #<Metabolite:0x00007fdb7097cc48>

3D SDF for #<Metabolite:0x00007fdb7097cc48>

3D-SDF for #<Metabolite:0x00007fdb7097cc48>

PDB for #<Metabolite:0x00007fdb7097cc48>

3D PDB for #<Metabolite:0x00007fdb7097cc48>

SMILES for #<Metabolite:0x00007fdb7097cc48>

INCHI for #<Metabolite:0x00007fdb7097cc48>

Structure for #<Metabolite:0x00007fdb7097cc48>

3D Structure for #<Metabolite:0x00007fdb7097cc48>