sulfuric acid methyl (1R,9R,10S,11R,12R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,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-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: 179503
• Molecular Formular: C46H60N4O13S
• Molecular Mass: 909.0526
• Monoisotopic Mass: 908.387759
• SMILES: c12c([nH]c3c1CCN1C[C@@H](C[C@]3(C(=O)OC)c3c(cc4c(c3)[C@@]35[C@@H](N4C)[C@]([C@@H]([C@]4(C3N(CC=C4)CC5)CC)OC(=O)C)(C(=O)OC)O)OC)C[C@](C1)(CC)O)cccc2.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1C4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
• InChI: InChI=1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37?,38-,39-,42+,43-,44-,45+,46+;/m1./s1
• InChIKey: KDQAABAKXDWYSZ-DBBOTOCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (1R,9R,10S,11R,12R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,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-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: sulfuric acid methyl (1R,9R,10S,11R,12R)-11-(acetyloxy)-12-ethyl-4-[(1S,13S,15S,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-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: Vincaleukoblastine Sulfate; (+)-Vinblastine Sulfate; Rozevin; VLB; Valban; Vinblastin; 29060-LE; Exal; Velban; Velbe; Vinblastine Sulfate

Database IDs

• CAS Number: 143-67-9
• PubChem SID: 164235413
• PubChem CID: 46783244

CALCULATED PROPERTIES

• Acid pKa: 10.869524
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.6706752
• LogD (pH = 7.4): 1.8057727
• Log P: 4.1831455
• Molar Refractivity: 222.4206 cm^3
• Polarizability: 87.76486 Å^3
• Polar Surface Area: 154.1 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V314000

Antitumor alkaloid isolated from periwinkle, Vinca rosea Linn., Apocynaceae; inhibits microtubule assembly. An antineoplastic.

REFERENCES

• Lu, C., et al.: Cancer Research, 39, 3575 (1979)
• Gobbi, P.G., et al.: J. Clin. Oncol., 14, 527 (1979)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs. Excip., 21, 611 (1979)