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

Superclasses: a macrocyclea porphyrina bilina phytobilina phycobilina 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 Formation (ΔfG in kcal/mol): 220.17213Inferred 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 [iron-sulfur] cluster ← biliverdin-IX-α + 4 a reduced ferredoxin [iron-sulfur] cluster + 4 H+

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


Beale84: Beale SI, Cornejo J (1984). "Enzymic Transformation of Biliverdin to Phycocyanobilin by Extracts of the Unicellular Red Alga Cyanidium caldarium." Plant Physiol 76(1);7-15. PMID: 16663825

Cornejo92: Cornejo J, Beale SI, Terry MJ, Lagarias JC (1992). "Phytochrome assembly. The structure and biological activity of 2(R),3(E)-phytochromobilin derived from phycobiliproteins." J Biol Chem 267(21);14790-8. PMID: 1634523

Lagarias95: Lagarias DM, Wu SH, Lagarias JC (1995). "Atypical phytochrome gene structure in the green alga Mesotaenium caldariorum." Plant Mol Biol 29(6);1127-42. PMID: 8616213

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

Terry95: Terry MJ, McDowell MT, Lagarias JC (1995). "(3Z)- and (3E)-phytochromobilin are intermediates in the biosynthesis of the phytochrome chromophore." J Biol Chem 270(19);11111-8. PMID: 7744741

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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
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