3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid hydrochloride

• ChemBase ID: 154785
• Molecular Formular: C33H35ClN4O6
• Molecular Mass: 619.1072
• Monoisotopic Mass: 618.22451254
• SMILES: Cc1c(c([nH]c1/C=C\1/C(=C(C(=O)N1)C)C=C)/C=C\1/C(=C(C(=N1)/C=C\1/C(=C(C(=O)N1)C=C)C)C)CCC(=O)O)CCC(=O)O.Cl
• Canonical SMILES: C=CC1=C(C)/C(=C/C2=N/C(=C\c3[nH]c(c(c3CCC(=O)O)C)/C=C/3\NC(=O)C(=C3C=C)C)/C(=C2C)CCC(=O)O)/NC1=O.Cl
• InChI: InChI=1S/C33H34N4O6.ClH/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;/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41);1H
• InChIKey: KTRFJVRKVQROKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid hydrochloride
• IUPAC Traditional name: biliverdin hydrochloride
• Synonyms: Biliverdin hydrochloride

Database IDs

• PubChem SID: 162248923
• PubChem CID: 71311981

CALCULATED PROPERTIES

• Acid pKa: 3.8685813
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.33365437
• LogD (pH = 7.4): -3.3118656
• Log P: 0.5727987
• Molar Refractivity: 169.3551 cm^3
• Polarizability: 61.570114 Å^3
• Polar Surface Area: 160.95 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C33H34N4O6 · HCl

DETAILS

Sigma Aldrich - 30891

Biochem/physiol Actions
Biliverdin is a linear tetrapyrrolic intermediate of heme degradation (heme catabolism) to bilirubin 1,2,3,4,5. The bile of amphibia and birds contains only biliverdine, no bilirubin. Biliverdin also shows antioxidant activities.6