methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-8-formyl-10-hydroxy-5-methoxy-4-[(5S,7S)-7-(methoxycarbonyl)-5-(2-oxobutyl)-1H,2H,3H,4H,5H,6H,7H,8H-azonino[5,4-b]indol-7-yl]-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

• ChemBase ID: 179507
• Molecular Formular: C45H54N4O10
• Molecular Mass: 810.93106
• Monoisotopic Mass: 810.38399395
• 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)CCNC[C@@H](C2)CC(=O)CC)C(=O)OC)c(c1)OC)C=O
• Canonical SMILES: CCC(=O)C[C@H]1CNCCc2c([C@@](C1)(C(=O)OC)c1cc3c(cc1OC)N([C@@H]1[C@@]43CCN3[C@H]4[C@@](CC)(C=CC3)[C@H]([C@]1(O)C(=O)OC)OC(=O)C)C=O)[nH]c1c2cccc1
• InChI: InChI=1S/C45H54N4O10/c1-7-28(52)20-27-23-44(40(53)57-5,36-30(14-17-46-24-27)29-12-9-10-13-33(29)47-36)32-21-31-34(22-35(32)56-4)49(25-50)38-43(31)16-19-48-18-11-15-42(8-2,37(43)48)39(59-26(3)51)45(38,55)41(54)58-6/h9-13,15,21-22,25,27,37-39,46-47,55H,7-8,14,16-20,23-24H2,1-6H3/t27-,37+,38-,39-,42-,43-,44+,45+/m1/s1
• InChIKey: GHCGXAFOOQYBDC-QPSORRKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-8-formyl-10-hydroxy-5-methoxy-4-[(5S,7S)-7-(methoxycarbonyl)-5-(2-oxobutyl)-1H,2H,3H,4H,5H,6H,7H,8H-azonino[5,4-b]indol-7-yl]-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)-11-(acetyloxy)-12-ethyl-8-formyl-10-hydroxy-5-methoxy-4-[(5S,7S)-7-(methoxycarbonyl)-5-(2-oxobutyl)-1H,2H,3H,4H,5H,6H,8H-azonino[5,4-b]indol-7-yl]-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: (2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-1-formyl-3-hydroxy-16-methoxy-15-[(5S,7S)-1,2,3,4,5,6,7,8-octahydro-7-(methoxycarbonyl)-5-(2-oxobutyl)azonino[5,4-b]indol-7-yl]aspidospermidine-3-carboxylic Acid Methyl Ester; Vincristine M1DISCONTINUED

Database IDs

• CAS Number: 910580-56-2
• PubChem SID: 164235417
• PubChem CID: 25141411

CALCULATED PROPERTIES

• Acid pKa: 10.9692335
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.683102
• LogD (pH = 7.4): -0.4531879
• Log P: 2.7280502
• Molar Refractivity: 217.237 cm^3
• Polarizability: 86.17776 Å^3
• Polar Surface Area: 176.8 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V314240

The selective metabolite of Vincristine by CYP3A5.

REFERENCES

• Eap, C., et al.: Eur. J. Clin. Pharmacol., 60, 231 (2004)
• Zhou, X., et al.: Anticancer Res., 14, 1017 (2004)
• Dantzig, A., et al.: Cancer Res., 56, 4171 (2004)
• Brown, H., et al.: Drug Metab. Dispos., 35, 293 (2004)
• Dennison, J., et al.: J. Pharmacol. E