3-(2-{[(2Z)-3-(2-carboxyethyl)-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-{[(2Z,3E)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

• ChemBase ID: 176708
• Molecular Formular: C33H38N4O6
• Molecular Mass: 586.67802
• Monoisotopic Mass: 586.27913496
• SMILES: C1(/C(=C\C)/C(=C/c2c(c(c([nH]2)/C=C\2/C(=C(C(=N2)/C=C\2/C(=C(C(=O)N2)CC)C)C)CCC(=O)O)CCC(=O)O)C)/NC1=O)C
• Canonical SMILES: CCC1=C(C)/C(=C/C2=N/C(=C\c3[nH]c(c(c3CCC(=O)O)C)/C=C/3\NC(=O)C(\C3=C/C)C)/C(=C2C)CCC(=O)O)/NC1=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)/b20-7+,26-13-,27-14-,28-15-
• InChIKey: INPDFIMLLXXDOQ-ZZEPTHGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-{[(2Z)-3-(2-carboxyethyl)-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-{[(2Z,3E)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• IUPAC Traditional name: 3-(2-{[(2Z)-3-(2-carboxyethyl)-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methylpyrrol-2-ylidene]methyl}-5-{[(2Z,3E)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• Synonyms: (3E)-18-Ethyl-3-ethylidene-1,2,3,19,22,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic Acid; (±)-Phycocyanobilin; rac-Phycocyanobilin

Database IDs

• CAS Number: 215871-76-4
• PubChem SID: 164232618
• PubChem CID: 54611329

CALCULATED PROPERTIES

• Acid pKa: 3.8558145
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.032794192
• LogD (pH = 7.4): -2.9335146
• Log P: 0.9512215
• Molar Refractivity: 169.5076 cm^3
• Polarizability: 62.058598 Å^3
• Polar Surface Area: 160.95 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P397650

Phycocyanobilin is an open-chain tetrapyrroles used as chromophores for the plant photoreceptor protein phytochrome.

REFERENCES

• Li, L., et al.: J. Biol. Chem., 267, 19204 (1992)
• Murphy, J., et al.: Photochem. Photobiol., 65, 750 (1992)
• Song, P., et al.: Plant Cell Environ., 20, 707 (1992)