3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

• ChemBase ID: 161981
• Molecular Formular: C33H36N4O6
• Molecular Mass: 584.66214
• Monoisotopic Mass: 584.26348489
• SMILES: C1(Cc2c(c(c([nH]2)/C=C\2/C(=C(C(=N2)O)C)C=C)C)CCC(=O)O)N=C(C(=C1CCC(=O)O)C)/C=C/1\N=C(C(=C1C)C=C)O
• Canonical SMILES: C=CC1=C(C)/C(=C/C2=NC(C(=C2C)CCC(=O)O)Cc2[nH]c(c(c2CCC(=O)O)C)/C=C/2\N=C(C(=C2C=C)C)O)/N=C1O
• 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/h7-8,13-14,28,35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-
• InChIKey: BQSLUCYCPLBAQC-IFADSCNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• IUPAC Traditional name: 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-5-hydroxy-3-methylpyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-5-hydroxy-4-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• Synonyms: 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetrametyl-1,19-dioxo-21H-biline-8,12-dipropanoic Acid; Bilirubin IXα; Bilirubin

Database IDs

• CAS Number: 635-65-4
• PubChem SID: 162256116
• PubChem CID: 5497144

CALCULATED PROPERTIES

• Acid pKa: 3.8731155
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 1.5902673
• LogD (pH = 7.4): -2.2654514
• Log P: 2.3919854
• Molar Refractivity: 169.0155 cm^3
• Polarizability: 61.579952 Å^3
• Polar Surface Area: 167.93 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Benzene; Chloroform; DMSO
• Apperance: Dark Orange Solid
• Melting Point: >220°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B385300

Principal pigment of bile and constituent of many biliary calculi.

REFERENCES

• Stenhagen, R., et al.: Biochem. J., 33, 1591 (1939)
• Gray, et al.: J. Chem. Soc., 2264, 2268 (1939)