methoxysulfonic acid methyl (1R,9R,10S,11R,12R,19R)-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-10,11-dihydroxy-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: 166129
• Molecular Formular: C45H58N4O13S
• Molecular Mass: 895.02602
• Monoisotopic Mass: 894.37210894
• SMILES: S(=O)(=O)(O)OC.[C@@]123[C@H]([C@@]([C@@H]([C@]4([C@@H]1N(CC2)CC=C4)CC)O)(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
• Canonical SMILES: COS(=O)(=O)O.COc1cc2N(C=O)[C@@H]3[C@@]4(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/C44H54N4O9.CH4O4S/c1-6-40(53)21-26-22-43(38(51)56-4,34-28(13-17-46(23-26)24-40)27-11-8-9-12-31(27)45-34)30-19-29-32(20-33(30)55-3)48(25-49)36-42(29)15-18-47-16-10-14-41(7-2,35(42)47)37(50)44(36,54)39(52)57-5;1-5-6(2,3)4/h8-12,14,19-20,25-26,35-37,45,50,53-54H,6-7,13,15-18,21-24H2,1-5H3;1H3,(H,2,3,4)/t26-,35+,36-,37-,40+,41-,42-,43+,44+;/m1./s1
• InChIKey: KLIAZUVLFVLIOU-FQXVZSFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methoxysulfonic acid methyl (1R,9R,10S,11R,12R,19R)-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-10,11-dihydroxy-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: methyl (1R,9R,10S,11R,12R,19R)-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-10,11-dihydroxy-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 methyl sulfate
• Synonyms: O4-Deacetyl-22-oxo-vincaleukoblastine Methosulfate; 4-Deacetyl Leurocristine Methosulfate; 4-Deacetylvincristine Methosulfate; 4-Desacetylvincristine Methosulfate; 4-Desacetyl Vincristine Methosulfate

Database IDs

• CAS Number: 3704-01-6
• PubChem SID: 162260262
• PubChem CID: 71315577

CALCULATED PROPERTIES

• Acid pKa: 10.879945
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.5924976
• LogD (pH = 7.4): 0.9191454
• Log P: 2.6870537
• Molar Refractivity: 212.3289 cm^3
• Polarizability: 83.99791 Å^3
• Polar Surface Area: 165.1 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: >300°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D288729

A metabolite of Vincristine in bile. Antitumor agent used against human colon carcinoma.

REFERENCES

• Houghton, J.A., et al.: Anal. Biochem., 134, 450 (1983)
• Sethi, V.S., et al.: Cancer Res., 45, 5386 (1983)
• Horton, J.K., et al.: Biochem. Pharmacol., 38, 1727 (1983)