methyl (1S,9S,10R,11S,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-11-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: 166052
• Molecular Formular: C44H54N4O8
• Molecular Mass: 766.92156
• Monoisotopic Mass: 766.39416471
• SMILES: [C@@]123[C@H]([C@H]([C@@H]([C@]4([C@@H]1N(CC2)CC=C4)CC)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: COC(=O)[C@H]1[C@H](O)[C@]2(CC)C=CCN3[C@@H]2[C@@]2([C@H]1N(C=O)c1c2cc(c(c1)OC)[C@]1(C[C@@H]2CN(CCc4c1[nH]c1c4cccc1)C[C@](C2)(O)CC)C(=O)OC)CC3
• InChI: InChI=1S/C44H54N4O8/c1-6-41(53)21-26-22-44(40(52)56-5,35-28(13-17-46(23-26)24-41)27-11-8-9-12-31(27)45-35)30-19-29-32(20-33(30)54-3)48(25-49)36-34(38(51)55-4)37(50)42(7-2)14-10-16-47-18-15-43(29,36)39(42)47/h8-12,14,19-20,25-26,34,36-37,39,45,50,53H,6-7,13,15-18,21-24H2,1-5H3/t26-,34-,36+,37+,39+,41+,42+,43+,44+/m1/s1
• InChIKey: RZVMMARIDNVUCW-OZXRLHGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,9S,10R,11S,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-11-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: methyl (1S,9S,10R,11S,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-11-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: 4-Deacetyl-3-deoxyvincristine; O4-Deacetyl-3-deoxy-22-oxo-vincaleukoblastine; 4-Deacetyl-3-deoxyleurocristine; 4-Desacetyl 3-Deoxy Vincristine

Database IDs

• CAS Number: 99435-53-7
• PubChem SID: 162260185
• PubChem CID: 71315530

CALCULATED PROPERTIES

• Acid pKa: 13.902978
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.3099554
• LogD (pH = 7.4): 1.214929
• Log P: 3.2785714
• Molar Refractivity: 211.0829 cm^3
• Polarizability: 83.36714 Å^3
• Polar Surface Area: 144.87 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288435

Degradation product of Vincristine (V314250)

REFERENCES

• Sethi, V., et al.: Cancer Res., 45, 5386 (1985)