methyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

• ChemBase ID: 166128
• Molecular Formular: C44H56N4O8
• Molecular Mass: 768.93744
• Monoisotopic Mass: 768.40981477
• SMILES: c1ccc2c(c1)c1c([nH]2)[C@](C[C@@H]2C[C@@](CN(CC1)C2)(O)CC)(c1c(cc2c(c1)C13[C@@H](N2C)[C@]([C@@H]([C@]2([C@@H]3N(CC1)CC=C2)CC)O)(C(=O)OC)O)OC)C(=O)OC
• Canonical SMILES: COc1cc2N(C)[C@@H]3C4(c2cc1[C@]1(C[C@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)O)(CC)C=CC1
• InChI: InChI=1S/C44H56N4O8/c1-7-40(52)22-26-23-43(38(50)55-5,34-28(14-18-47(24-26)25-40)27-12-9-10-13-31(27)45-34)30-20-29-32(21-33(30)54-4)46(3)36-42(29)16-19-48-17-11-15-41(8-2,35(42)48)37(49)44(36,53)39(51)56-6/h9-13,15,20-21,26,35-37,45,49,52-53H,7-8,14,16-19,22-25H2,1-6H3/t26?,35-,36+,37+,40-,41+,42?,43-,44-/m0/s1
• InChIKey: NDMPLJNOPCLANR-GKUSHNJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate
• IUPAC Traditional name: methyl (9R,10S,11R,12R,19R)-12-ethyl-4-[(1R,13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate
• Synonyms: O4-Deacetylvincaleukoblastine; 4-Deacetylvinblastine; Deacetylvinblastine; O4-Desacetylvinblastine; 4-Desacetyl Vinblastine Discontinued. See D288440

Database IDs

• CAS Number: 3352-69-0
• PubChem SID: 162260261
• PubChem CID: 71315532

CALCULATED PROPERTIES

• Acid pKa: 10.899763
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.9325186
• LogD (pH = 7.4): 1.5793723
• Log P: 3.74202
• Molar Refractivity: 213.2691 cm^3
• Polarizability: 83.92976 Å^3
• Polar Surface Area: 148.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Solid
• Melting Point: 189-191°C

DETAILS

Toronto Research Chemicals - D288728

A pro-drug of Vinblastine. Antitumor agent used for treatment of prostate cancer.

REFERENCES

• Raghavan, D., et al.: Eur. J. Cancer, 33, 566 (1997)
• Brady, S.F., et al.: J. Med. Chem., 45, 4706 (1997)