Metabolomics Structure Database

 
MW REGNO: 37047
Common Name:Bilirubin
Systematic 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
RefMet Name:Bilirubin
Synonyms: [PubChem Synonyms]
Exact Mass:
584.2635 (neutral)    Calculate m/z:
Formula:C33H36N4O6
InChIKey:BPYKTIZUTYGOLE-IFADSCNNSA-N
ClassyFire superclass:Organoheterocyclic compounds [C0000002]
ClassyFire class:Tetrapyrroles and derivatives [C0001455]
ClassyFire subclass:Bilirubins [C0001593]
ClassyFire direct parent:Bilirubins [C0001593]
MoNA MS spectra:View MS spectra
NP-MRD NMR spectra:View NMR spectra
SMILES:C=CC1=C(C)C(=O)N/C/1=C\c1c(C)c(CCC(=O)O)c(Cc2c(CCC(=O)O)c(C)c(/C=C\3/C(=C(C=C)C(=O)N3)C)[nH]2)[nH]1
Studies:Available studies (via RefMet name)

Select appropriate tab below to view additional details:

External database links:

PubChem CID:5280352
CHEBI ID:16990
HMDB ID:HMDB0000054
KEGG ID:C00486
Chemspider ID:4444055
METLIN ID:81
BMRB ID:bmse000627
MetaCyc ID:BILIRUBIN
NP-MRD ID(NMR):NP0000301
EPA CompTox DB:DTXCID20210821
Plant Metabolite Hub(Pmhub):MS000000291

Calculated physicochemical properties (?):

Heavy Atoms: 43  
Rings: 4  
Aromatic Rings: 2  
Rotatable Bonds: 12  
van der Waals Molecular volume: 568.00 Å3 molecule-1  
Toplogical Polar Sufrace Area: 164.38 Å2 molecule-1  
Hydrogen Bond Donors: 6  
Hydrogen Bond Acceptors: 6  
logP: 4.22  
Molar Refractivity: 163.68  
Fraction sp3 Carbons: 0.27  
sp3 Carbons: 9  

Human Pathway links:

HMDB and KEGG pathways containing this metabolite

REACTOME pathways containing this metabolite

References

LIPID MAPS classification: "Update of the LIPID MAPS comprehensive classification system for lipids", Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, and Dennis EA, J. Lipid Res. (2009) 50: S9-S14. DOI: 10.1194/jlr.R800095-JLR200
ClassyFire classification: "ClassyFire: automated chemical classification with a comprehensive, computable taxonomy", Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS, J. Cheminformatics (2016) 8:61. DOI: 10.1186/s13321-016-0174-y

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