CHEBI:26116 - phytochromobilin

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ChEBI Name phytochromobilin
ChEBI ID CHEBI:26116
Definition A member of the class of bilins which functions as the chromophore of light-sensing phytochromes in plants.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C33H36N4O6
Net Charge 0
Average Mass 584.673
Monoisotopic Mass 584.26348
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/h7-8,13-15,19,35H,2,9-12H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b20-7?,26-13-,27-14-,28-15-/t19-/m1/s1
InChIKey DKMLMZVDTGOEGU-MKLOKSPTSA-N
SMILES C(\C=1C(=C(\C(\N1)=C\C=2NC(=C(C2CCC(O)=O)C)/C=C/3\NC([C@@H](C3=C(C)[H])C)=O)CCC(=O)O)C)=C/4\NC(C(=C4C)C=C)=O
Roles Classification
Chemical Role(s): phytochrome chromophore
A chromophore that is a linear tetrapyrrolic prosthetic group covalently attached to a large soluble protein phytochrome. Light absorption by the phytochrome chromophore triggers photoconversion between two spectrally distinct forms of the photoreceptor: Pr, the red light absorbing form, and Pfr, the far-red light absorbing form.
Biological Role(s): cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
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ChEBI Ontology
Outgoing phytochromobilin (CHEBI:26116) has role cofactor (CHEBI:23357)
phytochromobilin (CHEBI:26116) has role phytochrome chromophore (CHEBI:82632)
phytochromobilin (CHEBI:26116) is a bilins (CHEBI:22869)
phytochromobilin (CHEBI:26116) is conjugate acid of phytochromobilin(2−) (CHEBI:189064)
Incoming S-phytochromobilin-L-cysteine (CHEBI:22069) has functional parent phytochromobilin (CHEBI:26116)
(3E)-phytochromobilin (CHEBI:146182) is a phytochromobilin (CHEBI:26116)
(3Z)-phytochromobilin (CHEBI:15619) is a phytochromobilin (CHEBI:26116)
phytochromobilin(2−) (CHEBI:189064) is conjugate base of phytochromobilin (CHEBI:26116)
IUPAC Name
3-{2-[(Z)-{3-(2-carboxyethyl)-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-4-methyl-2H-pyrrol-2-ylidene}methyl]-5-[(Z)-{(3Z,4R)-3-[(1Z)-ethylidene]-4-methyl-5-oxopyrrolidin-2-ylidene}methyl]-4-methyl-1H-pyrrol-3-yl}propanoic acid
Synonym Source
phytochromobilin ChEBI
Manual Xref Database
Phytochromobilins MetaCyc
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Citations Waiting for Citations Types Sources
11263892 PubMed citation Europe PMC
1634523 PubMed citation Europe PMC
18658149 PubMed citation Europe PMC
21192668 PubMed citation Europe PMC
24261565 PubMed citation Europe PMC
7744741 PubMed citation Europe PMC
Last Modified
17 February 2020