MetaCyc Compound: (2R,3Z)-phycocyanobilin

Superclasses: a macrocycle a porphyrin a bilin a phytobilin a phycobilin a phycocyanobilin

Phycocyanobilin is a blue pigment that belongs to the phycobilins. It is found in Cyanobacteria and in the chloroplasts of rhodophytes, glaucocystophytes, and some cryptomonads.

Phycocyanobilin is covalently linked to the phycobiliproteins allophycocyanin, phycocyanin, and phycoerythrocyanin by a thioether bond to conserved cysteine resudues.

Chemical Formula: C33H36N4O6

Molecular Weight: 584.67 Daltons

Monoisotopic Molecular Weight: 586.2791349732 Daltons

(2R,3Z)-phycocyanobilin compound structure

SMILES: CC=C1(C(C)C(NC1=CC4(=C(C)C(CCC([O-])=O)=C(C=C2(C(CCC([O-])=O)=C(C)C(=N2)C=C3(C(C)=C(CC)C(=O)N3)))N4))=O)

InChI: InChI=1S/C33H38N4O6/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/h7,13-15,19,35H,8-12H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/p-2/b20-7-,26-13-,27-14-,28-15-/t19-/m1/s1


Unification Links: ChEBI:57437 , PubChem:46224546

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 220.17213 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

phycocyanobilin biosynthesis , phycoviolobilin biosynthesis :
(2R,3Z)-phycocyanobilin → (2R,3E)-phycocyanobilin

Reactions known to produce the compound:

phycocyanobilin biosynthesis , phycoviolobilin biosynthesis :
(2R,3Z)-phycocyanobilin + 4 an oxidized ferredoxin ← biliverdin-IX-α + 4 a reduced ferredoxin + 4 H+

Revised 20-Mar-2013 by Caspi R , SRI International


Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Thu Oct 8, 2015, biocyc13.