(3R)-3,7-dihydroxy-3-({[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl]oxy}carbonyl)-7-methyloctanoic acid

• ChemBase ID: 165790
• Molecular Formular: C28H37NO9
• Molecular Mass: 531.59468
• Monoisotopic Mass: 531.24683177
• SMILES: O1COc2c1cc1c(c2)[C@H]2[C@@]3(N(CC1)CCC3)C=C([C@H]2OC(=O)C(CCCC(O)(C)C)(CC(=O)O)O)OC
• Canonical SMILES: COC1=C[C@]23[C@@H]([C@@H]1OC(=O)C(CC(=O)O)(CCCC(O)(C)C)O)c1cc4OCOc4cc1CCN3CCC2
• InChI: InChI=1S/C28H37NO9/c1-26(2,33)7-4-9-28(34,15-22(30)31)25(32)38-24-21(35-3)14-27-8-5-10-29(27)11-6-17-12-19-20(37-16-36-19)13-18(17)23(24)27/h12-14,23-24,33-34H,4-11,15-16H2,1-3H3,(H,30,31)/t23-,24-,27+,28-/m1/s1
• InChIKey: LRNKGNYRSLLFRU-KSZYUSJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3,7-dihydroxy-3-({[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^2,^6.0^6,^1^0.0^1^5,^1^9]icosa-1(20),4,13,15(19)-tetraen-3-yl]oxy}carbonyl)-7-methyloctanoic acid
• IUPAC Traditional name: (3R)-3,7-dihydroxy-3-({[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^2,^6.0^6,^1^0.0^1^5,^1^9]icosa-1(20),4,13,15(19)-tetraen-3-yl]oxy}carbonyl)-7-methyloctanoic acid
• Synonyms: Cephalotaxine 4-Hydrogen (2R)-2-Hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (Ester); 5'-Des-O-methylhomoharringtonine; 4'-Demethyl Homoharringtonine

Database IDs

• CAS Number: 98599-84-9
• PubChem SID: 162259923
• PubChem CID: 26499229

CALCULATED PROPERTIES

• Acid pKa: 3.6582208
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -0.9968721
• LogD (pH = 7.4): -0.9952285
• Log P: -0.9932348
• Molar Refractivity: 137.3058 cm^3
• Polarizability: 53.79535 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D231150

A metabolite of Homoharringtonine, a cytotoxic component of the evergreen plant Cephalotaxus harringtonia.

REFERENCES

• Powell, R., et al.: J. Pharm. Sci., 61, 1227 (1972)
• Ohnuma, T., et al.: J. Clin. Oncol., 3, 604 (1972)
• Scudiero, D., et al.: Cancer Res., 48, 4827 (1972)
• Zhou, D., et al.: Bull. Cancer, 82, 987 (1972)
• Kantarjian, H., et al.: Cancer, 92, 1591 (1972)