methyl (1R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-4-[(13S,15R)-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,16-pentaen-13-yl]-10-hydroxy-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: 160700
• Molecular Formular: C46H56N4O8
• Molecular Mass: 792.95884
• Monoisotopic Mass: 792.40981477
• SMILES: c12c([nH]c3c1CCN1C[C@H](C[C@]3(C(=O)OC)c3c(cc4c(c3)[C@@]35C(N4C)[C@]([C@@H]([C@]4([C@H]3N(CC=C4)CC5)CC)OC(=O)C)(C(=O)OC)O)OC)C=C(C1)CC)cccc2
• Canonical SMILES: CCC1=C[C@@H]2CN(C1)CCc1c([C@@](C2)(C(=O)OC)c2cc3c(cc2OC)N(C2[C@@]43CCN3[C@@H]4[C@@](CC)(C=CC3)[C@H]([C@]2(O)C(=O)OC)OC(=O)C)C)[nH]c2c1cccc2
• InChI: InChI=1S/C46H56N4O8/c1-8-28-21-29-24-45(41(52)56-6,37-31(15-19-49(25-28)26-29)30-13-10-11-14-34(30)47-37)33-22-32-35(23-36(33)55-5)48(4)39-44(32)17-20-50-18-12-16-43(9-2,38(44)50)40(58-27(3)51)46(39,54)42(53)57-7/h10-14,16,21-23,29,38-40,47,54H,8-9,15,17-20,24-26H2,1-7H3/t29-,38+,39?,40+,43+,44+,45-,46-/m0/s1
• InChIKey: FFRFGVHNKJYNOV-PCYZBDGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-4-[(13S,15R)-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9,16-pentaen-13-yl]-10-hydroxy-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 (1R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-4-[(13S,15R)-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9,16-pentaen-13-yl]-10-hydroxy-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: 3',4'-Didehydro-4'-deoxyvincaleukoblastine Disulfate Salt; (+)-Anhydrovinblastine Disulfate Salt; 3',4'-Anhydrovinblastine Disulfate Salt; 3',4'-Dehydroisoleurosine Disulfate Salt; 3',4'-Dehydrovinblastine Disulfate Salt; 3',4'-Didehydroisoleurosine Disulfate Salt; Anhydrovincaleukoblastine Disulfate Salt; F 81097 Disulfate Salt; Anhydro Vinblastine Disulfate Salt

Database IDs

• CAS Number: 81165-17-5
• PubChem SID: 162254835
• PubChem CID: 46780408

CALCULATED PROPERTIES

• Acid pKa: 10.868879
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.748637
• LogD (pH = 7.4): 2.7532218
• Log P: 4.936866
• Molar Refractivity: 221.7425 cm^3
• Polarizability: 86.89491 Å^3
• Polar Surface Area: 133.87 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: >220°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A659750

Anhydrovinblastine showed significant cytotoxic potential against a panel of human cancer cell lines and significant activity against the human H460 non-small cell lung carcinoma tumor xenograph in mice.

REFERENCES

• Koiso, Y., et al.: J. Antibiot., 51, 418 (1998)
• Olver, I., et al.: Eur. J. Cancer, 43, 1829 (1998)
• Shao, Y., et al.: Bioorg. Med. Chem., 15, 5061 (2007).