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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:42:37 UTC

Update Date

2021-10-01 19:42:26 UTC

HMDB ID

HMDB0249207

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bilin

Description

Bilin belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next. Based on a literature review a significant number of articles have been published on Bilin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bilin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bilin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249207
     RDKit          3D
Bilin
 37 40  0  0  0  0  0  0  0  0999 V2000
    7.4091   -0.9490   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0761   -0.8847   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7015    0.5026   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585    1.1155   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    0.5716   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    1.3783   -0.0072 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515    0.6195    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014    1.0744    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723    0.1572    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351   -0.8959    1.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -1.4524    1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.7570    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -1.0774   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5062   -0.1059   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8855   -0.2458   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3153    0.9951   -0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2651    1.9602   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258    1.2829   -0.3262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    0.2134   -0.0282 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -0.7597    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.7775    0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9332    1.2276   -0.7134 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8899    0.3934   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9632   -1.8830   -0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -1.7480   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5925    2.2322   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3691    2.1332    0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.2274    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9309   -2.3052    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9208   -2.1110   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4331   -1.1784   -0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3297    1.2536   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3797    3.0340   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398    0.8973   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.6608    0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -1.6698    0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9372    0.6467   -0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
  7 20  1  0
 20 21  2  0
  3 22  1  0
 22 23  2  0
 23  1  1  0
 21  5  1  0
 19  9  1  0
 18 14  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END


  Mrv1652309112105422D          

 23 26  0  0  0  0            999 V2000
   -4.4640   -5.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7189   -4.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515   -4.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515   -3.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370   -3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2508   -2.3710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438   -2.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4182   -0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6731    0.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    0.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3382    0.0062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7201    1.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4738    1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0258    2.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    2.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064    2.5491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313   -2.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -3.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840   -4.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -5.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 14 12  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249207

> <DATABASE_NAME>
hmdb

> <SMILES>
N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H14N4/c1-3-14(20-9-1)11-16-5-7-18(22-16)13-19-8-6-17(23-19)12-15-4-2-10-21-15/h1-13,22H

> <INCHI_KEY>
PPRBOEHFGAHFGC-UHFFFAOYSA-N

> <FORMULA>
C19H14N4

> <MOLECULAR_WEIGHT>
298.349

> <EXACT_MASS>
298.121846467

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
33.32769172507643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2H-pyrrol-2-ylidene)methyl]-2-({5-[(2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl}methylidene)-2H-pyrrole

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
1.6565903879999997

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.083981153923347

> <JCHEM_PKA_STRONGEST_BASIC>
8.521089231949423

> <JCHEM_POLAR_SURFACE_AREA>
52.87

> <JCHEM_REFRACTIVITY>
100.94939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(pyrrol-2-ylidenemethyl)-5-{[5-(pyrrol-2-ylidenemethyl)-1H-pyrrol-2-yl]methylidene}pyrrole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249207
     RDKit          3D
Bilin
 37 40  0  0  0  0  0  0  0  0999 V2000
    7.4091   -0.9490   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0761   -0.8847   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7015    0.5026   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585    1.1155   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    0.5716   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    1.3783   -0.0072 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515    0.6195    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014    1.0744    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723    0.1572    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351   -0.8959    1.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -1.4524    1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.7570    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -1.0774   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5062   -0.1059   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8855   -0.2458   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3153    0.9951   -0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2651    1.9602   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258    1.2829   -0.3262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    0.2134   -0.0282 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -0.7597    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.7775    0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9332    1.2276   -0.7134 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8899    0.3934   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9632   -1.8830   -0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -1.7480   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5925    2.2322   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3691    2.1332    0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.2274    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9309   -2.3052    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9208   -2.1110   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4331   -1.1784   -0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3297    1.2536   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3797    3.0340   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398    0.8973   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.6608    0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -1.6698    0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9372    0.6467   -0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
  7 20  1  0
 20 21  2  0
  3 22  1  0
 22 23  2  0
 23  1  1  0
 21  5  1  0
 19  9  1  0
 18 14  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -8.333 -10.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.809  -9.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.563  -8.267   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.563  -6.727   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.229  -5.957   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -6.068  -4.426   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -4.562  -4.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.935  -2.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.841  -1.453   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.381  -1.453   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.856   0.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.611   0.917   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.365   0.012   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -5.611   2.457   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.944   3.227   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.351   2.600   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.382   3.745   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.612   5.079   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -7.105   4.758   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -3.792  -5.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.822  -6.584   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -6.317  -9.173   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -6.793 -10.637   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20    7   21                                                       
CONECT   21   20    5                                                       
CONECT   22    3   23                                                       
CONECT   23   22    1                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0249207
HETATM    1  C1  UNL     1       7.409  -0.949  -0.561  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.076  -0.885  -0.363  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.702   0.503  -0.450  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.559   1.115  -0.339  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.258   0.572  -0.084  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.208   1.378  -0.007  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.052   0.619   0.248  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.201   1.074   0.374  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.272   0.157   0.638  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.335  -0.896   1.530  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.603  -1.452   1.355  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.284  -0.757   0.389  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.640  -1.077  -0.038  1.00  0.00           C  
HETATM   14  C13 UNL     1      -5.506  -0.106  -0.360  1.00  0.00           C  
HETATM   15  C14 UNL     1      -6.886  -0.246  -0.803  1.00  0.00           C  
HETATM   16  C15 UNL     1      -7.315   0.995  -0.994  1.00  0.00           C  
HETATM   17  C16 UNL     1      -6.265   1.960  -0.692  1.00  0.00           C  
HETATM   18  N2  UNL     1      -5.226   1.283  -0.326  1.00  0.00           N  
HETATM   19  N3  UNL     1      -2.454   0.213  -0.028  1.00  0.00           N  
HETATM   20  C17 UNL     1       1.486  -0.760   0.324  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.824  -0.777   0.121  1.00  0.00           C  
HETATM   22  N4  UNL     1       6.933   1.228  -0.713  1.00  0.00           N  
HETATM   23  C19 UNL     1       7.890   0.393  -0.773  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.963  -1.883  -0.549  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.486  -1.748  -0.184  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.592   2.232  -0.460  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.369   2.133   0.271  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.583  -1.227   2.227  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.931  -2.305   1.932  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.921  -2.111  -0.088  1.00  0.00           H  
HETATM   31  H8  UNL     1      -7.433  -1.178  -0.943  1.00  0.00           H  
HETATM   32  H9  UNL     1      -8.330   1.254  -1.335  1.00  0.00           H  
HETATM   33  H10 UNL     1      -6.380   3.034  -0.774  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.740   0.897  -0.777  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.913  -1.661   0.497  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.386  -1.670   0.128  1.00  0.00           H  
HETATM   37  H14 UNL     1       8.937   0.647  -0.960  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    6   21
CONECT    6    7
CONECT    7    8    8   20
CONECT    8    9   27
CONECT    9   10   10   19
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   19
CONECT   13   14   14   30
CONECT   14   15   18
CONECT   15   16   16   31
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   19   34
CONECT   20   21   21   35
CONECT   21   36
CONECT   22   23   23
CONECT   23   37
END

HMDB0249207
     RDKit          3D
Bilin
 37 40  0  0  0  0  0  0  0  0999 V2000
    7.4091   -0.9490   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0761   -0.8847   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7015    0.5026   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585    1.1155   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    0.5716   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082    1.3783   -0.0072 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515    0.6195    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014    1.0744    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723    0.1572    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3351   -0.8959    1.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -1.4524    1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2839   -0.7570    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -1.0774   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5062   -0.1059   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8855   -0.2458   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3153    0.9951   -0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2651    1.9602   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258    1.2829   -0.3262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    0.2134   -0.0282 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -0.7597    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.7775    0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9332    1.2276   -0.7134 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8899    0.3934   -0.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9632   -1.8830   -0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4864   -1.7480   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5925    2.2322   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3691    2.1332    0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.2274    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9309   -2.3052    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9208   -2.1110   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4331   -1.1784   -0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3297    1.2536   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3797    3.0340   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398    0.8973   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.6608    0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -1.6698    0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9372    0.6467   -0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
  7 20  1  0
 20 21  2  0
  3 22  1  0
 22 23  2  0
 23  1  1  0
 21  5  1  0
 19  9  1  0
 18 14  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄N₄

Average Molecular Weight

298.349

Monoisotopic Molecular Weight

298.121846467

IUPAC Name

5-[(2H-pyrrol-2-ylidene)methyl]-2-({5-[(2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl}methylidene)-2H-pyrrole

Traditional Name

2-(pyrrol-2-ylidenemethyl)-5-{[5-(pyrrol-2-ylidenemethyl)-1H-pyrrol-2-yl]methylidene}pyrrole

CAS Registry Number

Not Available

SMILES

N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1

InChI Identifier

InChI=1S/C19H14N4/c1-3-14(20-9-1)11-16-5-7-18(22-16)13-19-8-6-17(23-19)12-15-4-2-10-21-15/h1-13,22H

InChI Key

PPRBOEHFGAHFGC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Not Available

Direct Parent

Tetrapyrroles and derivatives

Alternative Parents

Substituents

Tetrapyrrole skeleton
Dipyrrin
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

bilin (CHEBI:35798 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.68	ALOGPS
logP	1.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	15.08	ChemAxon
pKa (Strongest Basic)	8.52	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.87 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.95 m³·mol⁻¹	ChemAxon
Polarizability	33.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	166.831	30932474
DeepCCS	[M-H]-	164.473	30932474
DeepCCS	[M-2H]-	198.008	30932474
DeepCCS	[M+Na]+	173.235	30932474
AllCCS	[M+H]+	180.2	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	183.8	32859911
AllCCS	[M+Na]+	184.9	32859911
AllCCS	[M-H]-	179.4	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	179.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.0979 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2327.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	324.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	420.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	435.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1330.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	416.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1204.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	382.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	358.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bilin	N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	4467.6	Standard polar	33892256
Bilin	N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	3576.8	Standard non polar	33892256
Bilin	N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	3524.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bilin,1TMS,isomer #1	C[Si](C)(C)N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	3580.8	Semi standard non polar	33892256
Bilin,1TMS,isomer #1	C[Si](C)(C)N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	3209.9	Standard non polar	33892256
Bilin,1TMS,isomer #1	C[Si](C)(C)N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	4253.9	Standard polar	33892256
Bilin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	3706.9	Semi standard non polar	33892256
Bilin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	3390.5	Standard non polar	33892256
Bilin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(C=C2C=CC=N2)=CC=C1C=C1C=CC(C=C2C=CC=N2)=N1	4371.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bilin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-2690000000-57409f605439fcc87c83	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bilin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilin 10V, Positive-QTOF	splash10-0002-0090000000-e59d46dadb94a13b5261	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilin 20V, Positive-QTOF	splash10-0002-0090000000-76dd062bd592a8528d28	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilin 40V, Positive-QTOF	splash10-00di-0090000000-028e3f6720730d65748c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilin 10V, Negative-QTOF	splash10-0002-0090000000-9022dcd8cc9c89674bc8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilin 20V, Negative-QTOF	splash10-0002-0090000000-da3d4c8b446a4ba49597	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bilin 40V, Negative-QTOF	splash10-000t-0490000000-0cb2654601af6d55eae9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5256808

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bilin

METLIN ID

Not Available

PubChem Compound

6857471

PDB ID

Not Available

ChEBI ID

35798

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Apolipoprotein D

General function:: Not Available
Specific function:: APOD occurs in the macromolecular complex with lecithin-cholesterol acyltransferase. It is probably involved in the transport and binding of bilin. Appears to be able to transport a variety of ligands in a number of different contexts.
Gene Name:: APOD
Uniprot ID:: P05090
Molecular weight:: 21275.37

Showing metabocard for Bilin (HMDB0249207)

MOL for HMDB0249207 (Bilin)

3D MOL for HMDB0249207 (Bilin)

3D SDF for HMDB0249207 (Bilin)

3D-SDF for HMDB0249207 (Bilin)

PDB for HMDB0249207 (Bilin)

3D PDB for HMDB0249207 (Bilin)

SMILES for HMDB0249207 (Bilin)

INCHI for HMDB0249207 (Bilin)

Structure for HMDB0249207 (Bilin)

3D Structure for HMDB0249207 (Bilin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes