biliverdin   

GtoPdb Ligand ID: 5153

Comment: There is some ambiguity in the literature and on online resources as to the exact stereochemisitry of biliverdin. The structure shown here matches that linked to above in PubChem, but may be different to that shown in the other resources linked to. Other common representations are: CID 5280353, CID 6183357 and CID 5315455.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 160.95
Molecular weight 582.25
XLogP 2.71
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES C=CC1=C(C)C(=NC1=O)C=c1[nH]c(=Cc2[nH]c(c(c2CCC(=O)O)C)C=C2NC(=O)C(=C2C=C)C)c(c1C)CCC(=O)O
Isomeric SMILES C=CC1=C(C)C(=NC1=O)/C=c\1/[nH]/c(=C\c2[nH]c(c(c2CCC(=O)O)C)/C=C/2\NC(=O)C(=C2C=C)C)/c(c1C)CCC(=O)O
InChI 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/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)/b24-13+,27-14-,28-15-
InChI Key RCNSAJSGRJSBKK-YKSNQIBWSA-N
Classification
Compound class Metabolite or derivative
IUPAC Name
3-[2-[(Z)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-2-ylidene]methyl]-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
Database Links
CAS Registry No. 114-25-0
ChEBI CHEBI:17033
ChEMBL Ligand CHEMBL455477
GtoPdb PubChem SID 178101845
PubChem CID 5353439
Search Google for chemical match using the InChIKey RCNSAJSGRJSBKK-YKSNQIBWSA-N
Search Google for chemicals with the same backbone RCNSAJSGRJSBKK
Search UniChem for chemical match using the InChIKey RCNSAJSGRJSBKK-YKSNQIBWSA-N
Search UniChem for chemicals with the same backbone RCNSAJSGRJSBKK
Wikipedia Biliverdin