CHEBI:16990 - bilirubin

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ChEBI Name bilirubin
ChEBI ID CHEBI:16990
Definition A member of the class of biladienes that is a linear tetrapyrrole, product of heme degradation. It is produced in the reticuloendothelial system by the reduction of biliverdin and transported to the liver as a complex with serum albumin.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3099, CHEBI:13898, CHEBI:22870
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Formula C33H36N4O6
Net Charge 0
Average Mass 584.66230
Monoisotopic Mass 584.263
InChI 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-
InChIKey BPYKTIZUTYGOLE-IFADSCNNSA-N
SMILES CC1=C(C=C)\C(NC1=O)=C\c1[nH]c(Cc2[nH]c(\C=C3NC(=O)C(C=C)=C/3C)c(C)c2CCC(O)=O)c(CCC(O)=O)c1C
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:9606) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bilirubin (CHEBI:16990) has role antioxidant (CHEBI:22586)
bilirubin (CHEBI:16990) has role human metabolite (CHEBI:77746)
bilirubin (CHEBI:16990) has role mouse metabolite (CHEBI:75771)
bilirubin (CHEBI:16990) is a biladienes (CHEBI:36735)
bilirubin (CHEBI:16990) is a dicarboxylic acid (CHEBI:35692)
bilirubin (CHEBI:16990) is conjugate acid of bilirubin(2−) (CHEBI:57977)
Incoming bilirubin(2−) (CHEBI:57977) is conjugate base of bilirubin (CHEBI:16990)
IUPAC Name
bilirubin
Synonyms Sources
1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid ChemIDplus
2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid ChemIDplus
2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid IUPAC
8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione JCBN
Bilirubin KEGG COMPOUND
bilirubin IXα ChEBI
bilirubin(Z,Z) ChEBI
Database Links Databases
Bilirubin Wikipedia
BILIRUBIN MetaCyc
C00029828 KNApSAcK
C00486 KEGG COMPOUND
HMDB00054 HMDB
View more database links
Registry Numbers Types Sources
411033 Gmelin Registry Number Gmelin
635-65-4 CAS Registry Number ChemIDplus
74376 Reaxys Registry Number Reaxys
74376 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
12799017 PubMed citation Europe PMC
18442622 PubMed citation Europe PMC
23763371 PubMed citation Europe PMC
9587403 PubMed citation Europe PMC
Last Modified
10 October 2016