MiMeDB: Showing metabocard for biliverdin IXalpha (MMDBc0055782)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:06:12 UTC

Update Date

2022-08-12 20:09:27 UTC

Metabolite ID

MMDBc0055782

Metabolite Identification

Common Name

biliverdin IXalpha

Description

biliverdin(2-) belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. biliverdin(2-) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on biliverdin(2-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222062D          

 46 49  0  0  0  0            999 V2000
   10.4000   -2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5093    7.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6758    5.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655    3.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7217    1.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8635   -3.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0645   -1.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237    6.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1779    2.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2696    2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    2.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841    2.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1211    4.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1671   -0.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8176    1.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8912    5.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9786    3.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9371    1.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6920   -2.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2440   -1.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237    6.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8924    2.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2696    1.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7856    3.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6821    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6362    4.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8315   -1.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6461    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6022    1.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    2.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841    3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9383   -2.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563    5.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981    2.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8571    0.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8112    4.9051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0245   -1.2828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    1.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345    2.4919    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.2696    4.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6986    4.0544    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.2238   -2.5158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7717    5.9446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416    4.3239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9875   -0.2714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2045    0.7974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  8  2  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 16  3  1  0  0  0  0
 17  4  1  0  0  0  0
 18  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20  7  1  0  0  0  0
 20 19  2  0  0  0  0
 21  8  1  0  0  0  0
 21 16  2  0  0  0  0
 22  9  1  0  0  0  0
 22 17  2  0  0  0  0
 23 10  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 25 14  1  0  0  0  0
 25 18  2  0  0  0  0
 26 13  2  0  0  0  0
 26 16  1  0  0  0  0
 27 14  2  0  0  0  0
 27 20  1  0  0  0  0
 28 15  2  0  0  0  0
 28 22  1  0  0  0  0
 29 15  1  0  0  0  0
 29 23  2  0  0  0  0
 30 11  1  0  0  0  0
 31 12  1  0  0  0  0
 32 19  1  0  0  0  0
 33 21  1  0  0  0  0
 34 24  2  0  0  0  0
 34 28  1  0  0  0  0
 35 25  1  0  0  0  0
 35 29  1  0  0  0  0
 36 26  1  0  0  0  0
 36 33  2  0  0  0  0
 37 27  1  0  0  0  0
 37 32  2  0  0  0  0
 38 30  2  0  0  0  0
 39 30  1  0  0  0  0
 40 31  2  0  0  0  0
 41 31  1  0  0  0  0
 42 32  1  0  0  0  0
 43 33  1  0  0  0  0
 44 13  1  0  0  0  0
 45 14  1  0  0  0  0
 46 15  1  0  0  0  0
M  CHG  2  39  -1  41  -1
M  END


  Mrv1652306172222062D          

 46 49  0  0  0  0            999 V2000
   10.4000   -2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5093    7.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6758    5.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655    3.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7217    1.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8635   -3.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0645   -1.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237    6.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1779    2.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2696    2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634    2.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841    2.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1211    4.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1671   -0.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8176    1.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8912    5.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9786    3.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9371    1.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6920   -2.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2440   -1.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237    6.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8924    2.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2696    1.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7856    3.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6821    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6362    4.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8315   -1.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6461    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6022    1.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    2.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841    3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9383   -2.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563    5.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981    2.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8571    0.3098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8112    4.9051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0245   -1.2828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    1.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345    2.4919    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.2696    4.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6986    4.0544    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.2238   -2.5158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7717    5.9446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416    4.3239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9875   -0.2714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2045    0.7974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  8  2  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 16  3  1  0  0  0  0
 17  4  1  0  0  0  0
 18  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20  7  1  0  0  0  0
 20 19  2  0  0  0  0
 21  8  1  0  0  0  0
 21 16  2  0  0  0  0
 22  9  1  0  0  0  0
 22 17  2  0  0  0  0
 23 10  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 25 14  1  0  0  0  0
 25 18  2  0  0  0  0
 26 13  2  0  0  0  0
 26 16  1  0  0  0  0
 27 14  2  0  0  0  0
 27 20  1  0  0  0  0
 28 15  2  0  0  0  0
 28 22  1  0  0  0  0
 29 15  1  0  0  0  0
 29 23  2  0  0  0  0
 30 11  1  0  0  0  0
 31 12  1  0  0  0  0
 32 19  1  0  0  0  0
 33 21  1  0  0  0  0
 34 24  2  0  0  0  0
 34 28  1  0  0  0  0
 35 25  1  0  0  0  0
 35 29  1  0  0  0  0
 36 26  1  0  0  0  0
 36 33  2  0  0  0  0
 37 27  1  0  0  0  0
 37 32  2  0  0  0  0
 38 30  2  0  0  0  0
 39 30  1  0  0  0  0
 40 31  2  0  0  0  0
 41 31  1  0  0  0  0
 42 32  1  0  0  0  0
 43 33  1  0  0  0  0
 44 13  1  0  0  0  0
 45 14  1  0  0  0  0
 46 15  1  0  0  0  0
M  CHG  2  39  -1  41  -1
M  END
> <DATABASE_ID>
MMDBc0055782

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C1=C(C)C(CCC([O-])=O)=C(N1)C(\[H])=C1/N=C(/C(/[H])=C2\N=C(O)C(C=C)=C2C)C(C)=C1CCC([O-])=O)=C1\N=C(O)C(C)=C1C=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H34N4O6/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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/p-2/b26-13-,27-14-,28-15-

> <INCHI_KEY>
QBUVFDKTZJNUPP-BBROENKCSA-L

> <FORMULA>
C33H32N4O6

> <MOLECULAR_WEIGHT>
580.642

> <EXACT_MASS>
580.233281926

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
64.59322760570652

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2Z)-2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methylidene}-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-3-yl]propanoate

> <JCHEM_LOGP>
1.6758005184100744

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.526795829768361

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7635005913923902

> <JCHEM_PKA_STRONGEST_BASIC>
5.334341299365738

> <JCHEM_POLAR_SURFACE_AREA>
173.58999999999997

> <JCHEM_REFRACTIVITY>
192.07270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2Z)-2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methylidene}-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methylpyrrol-2-ylidene]methyl}-4-methylpyrrol-3-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      19.413  -4.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.284  13.836   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.328  11.097   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.016   7.214   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.147   2.519   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.545  -6.059   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.787  -3.569   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.618  13.066   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.665   3.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.437   4.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.332   4.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.770   5.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.293   7.910   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.112  -0.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.726   2.519   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.864  10.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.160   6.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.683   2.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.225  -4.552   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.255  -3.408   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.618  11.526   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.999   4.652   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.437   2.948   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.666   6.503   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.207   0.578   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.388   9.156   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.485  -2.074   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.406   4.025   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.191   2.043   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.998   3.882   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.770   6.798   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.818  -3.926   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.372  10.621   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      13.436   5.170   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      14.667   0.578   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0      10.848   9.156   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0      14.979  -2.395   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0       6.998   2.342   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.664   4.652   0.000  0.00  0.00           O-1
HETATM   40  O   UNK     0      15.437   7.568   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      18.104   7.568   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0      13.484  -4.696   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       8.907  11.097   0.000  0.00  0.00           O+0
HETATM   44  H   UNK     0      14.824   8.071   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      18.643  -0.507   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      11.582   1.488   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7    1   20                                                       
CONECT    8    2   21                                                       
CONECT    9   11   22                                                       
CONECT   10   12   23                                                       
CONECT   11    9   30                                                       
CONECT   12   10   31                                                       
CONECT   13   24   26   44                                                  
CONECT   14   25   27   45                                                  
CONECT   15   28   29   46                                                  
CONECT   16    3   21   26                                                  
CONECT   17    4   22   24                                                  
CONECT   18    5   23   25                                                  
CONECT   19    6   20   32                                                  
CONECT   20    7   19   27                                                  
CONECT   21    8   16   33                                                  
CONECT   22    9   17   28                                                  
CONECT   23   10   18   29                                                  
CONECT   24   13   17   34                                                  
CONECT   25   14   18   35                                                  
CONECT   26   13   16   36                                                  
CONECT   27   14   20   37                                                  
CONECT   28   15   22   34                                                  
CONECT   29   15   23   35                                                  
CONECT   30   11   38   39                                                  
CONECT   31   12   40   41                                                  
CONECT   32   19   37   42                                                  
CONECT   33   21   36   43                                                  
CONECT   34   24   28                                                       
CONECT   35   25   29                                                       
CONECT   36   26   33                                                       
CONECT   37   27   32                                                       
CONECT   38   30                                                            
CONECT   39   30                                                            
CONECT   40   31                                                            
CONECT   41   31                                                            
CONECT   42   32                                                            
CONECT   43   33                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

Synonyms

Value	Source
Biliverdin dianion	ChEBI
Biliverdin ixalpha	ChEBI

Molecular Formula

C₃₃H₃₂N₄O₆

Average Mass

580.642

Monoisotopic Mass

580.233281926

IUPAC Name

3-[(2Z)-2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methylidene}-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-3-yl]propanoate

Traditional Name

3-[(2Z)-2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methylidene}-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methylpyrrol-2-ylidene]methyl}-4-methylpyrrol-3-yl]propanoate

CAS Registry Number

Not Available

SMILES

[H]\C(C1=C(C)C(CCC([O-])=O)=C(N1)C(\[H])=C1/N=C(/C(/[H])=C2\N=C(O)C(C=C)=C2C)C(C)=C1CCC([O-])=O)=C1\N=C(O)C(C)=C1C=C

InChI Identifier

InChI=1S/C33H34N4O6/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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/p-2/b26-13-,27-14-,28-15-

InChI Key

QBUVFDKTZJNUPP-BBROENKCSA-L

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
Cyclic carboximidic acid
Heteroaromatic compound
Ketimine
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid dianion (CHEBI:57991 )
linear tetrapyrrole anion (CHEBI:57991 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.68	ChemAxon
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	5.33	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	173.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	192.07 m³·mol⁻¹	ChemAxon
Polarizability	64.59 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

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014058	Bilirubin	biliverdin IXalpha	Bilirubin oxidase	Oxidation	RHEA	34755880
MMDBr0014142	heme b	biliverdin IXalpha	Heme-degrading monooxygenase	Oxygenation	RHEA	34755880
MMDBr0024342	Tetra-mu3-sulfido-tetrairon(2+)	Hydrogen Ion	15,16-dihydrobiliverdin:ferredoxin oxidoreductase	Redox reaction	RHEA	34755880
MMDBr0024499	di-mu-Sulfido-diiron(2+)	Hydrogen Ion	Phycocyanobilin:ferredoxin oxidoreductase	Redox reaction	RHEA	34755880
MMDBr0024793	Tetra-mu3-sulfido-tetrairon(2+)	Hydrogen Ion	Phycoerythrobilin synthase	Synthesis	RHEA	34755880
MMDBr0025585	Hydrogen Ion	biliverdin IXalpha	F420H(2)-dependent biliverdin reductase	Reduction	RHEA	34755880

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
Eukaryota/Fungi	Ascomycota	1
Bacteria	Firmicutes	24	Human feces; Human ; Catfish
Bacteria	Actinobacteria	1
Bacteria	Proteobacteria	1
Bacteria	Cyanobacteria	1
Bacteria	nah	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26330996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

57991

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for biliverdin IXalpha (MMDBc0055782)

MOL for #<Metabolite:0x00007f5a8d3c6bf0>

3D MOL for #<Metabolite:0x00007f5a8d3c6bf0>

3D SDF for #<Metabolite:0x00007f5a8d3c6bf0>

3D-SDF for #<Metabolite:0x00007f5a8d3c6bf0>

PDB for #<Metabolite:0x00007f5a8d3c6bf0>

3D PDB for #<Metabolite:0x00007f5a8d3c6bf0>

SMILES for #<Metabolite:0x00007f5a8d3c6bf0>

INCHI for #<Metabolite:0x00007f5a8d3c6bf0>

Structure for #<Metabolite:0x00007f5a8d3c6bf0>

3D Structure for #<Metabolite:0x00007f5a8d3c6bf0>