sulfuric acid methyl (1R,9R,10S,11S,12R,19R)-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]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

• ChemBase ID: 179508
• Molecular Formular: C46H58N4O14S
• Molecular Mass: 923.03612
• Monoisotopic Mass: 922.36702356
• SMILES: [C@@]123[C@H]([C@@]([C@H]([C@]4([C@@H]1N(CC2)CC=C4)CC)OC(=O)C)(O)C(=O)OC)N(c1c3cc([C@@]2(c3c(c4c([nH]3)cccc4)CCN3C[C@@](C[C@H](C2)C3)(CC)O)C(=O)OC)c(c1)OC)C=O.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC
• InChI: InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28-,37+,38-,39+,42+,43-,44-,45+,46+;/m1./s1
• InChIKey: AQTQHPDCURKLKT-VPZGPLCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (1R,9R,10S,11S,12R,19R)-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]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• IUPAC Traditional name: sulfuric acid methyl (1R,9R,10S,11S,12R,19R)-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]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• Synonyms: NSC 67574; Novopharm; Oncovin; Onkovin; VCR Sulfate; Vincasar PFS; Vincrisul; Vincristine Sulfate; 22-Oxovincaleukoblastine Sulfate; Leurocristine Sulfate; Kyocristine; Lilly 37231

Database IDs

• CAS Number: 2068-78-2
• PubChem SID: 164235418
• PubChem CID: 71752951

CALCULATED PROPERTIES

• Acid pKa: 10.849017
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.3829613
• LogD (pH = 7.4): 1.1448158
• Log P: 3.128179
• Molar Refractivity: 221.4804 cm^3
• Polarizability: 87.836975 Å^3
• Polar Surface Area: 171.17 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: White Solid
• Melting Point: >230°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - V314250

An antitumor alkaloid isolated from Vinca rosea Linn. An antineoplastic.

REFERENCES

• Burns, J.H., et al.: Anal. Profiles Drug Subs., 1, 463 (1972)
• Owellen, D., et al.: J. Med. Chem., 15, 894 (1972)