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CHEBI:26116 - phytochromobilin

ChEBI IDCHEBI:26116
ChEBI Namephytochromobilin
Stars
DefinitionA member of the class of bilins which functions as the chromophore of light-sensing phytochromes in plants.
Last Modified17 February 2020
DownloadsMolfile
FormulaC33H36N4O6
Net Charge0
Average Mass584.673
Monoisotopic Mass584.26348
SMILES[H]C(C)=C1/C(=C/c2nc(/C=C3\N=C(/C=C4\NC(=O)C(C=C)=C4C)C(C)=C3CCC(=O)O)c(CCC(=O)O)c2C)NC(=O)[C@@H]1C
InChIInChI=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
InChIKeyDKMLMZVDTGOEGU-MKLOKSPTSA-N
Roles Classification
Chemical Role:
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:
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).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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
phytochromobilinChEBI
Manual XrefsDatabases
PhytochromobilinsMetaCyc
Citations