methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-8-formyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

• ChemBase ID: 169402
• Molecular Formular: C46H54N4O10
• Molecular Mass: 822.94176
• Monoisotopic Mass: 822.38399395
• 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)CCN3C[C@]4([C@@H]([C@H](C2)C3)O4)CC)C(=O)OC)c(c1)OC)C=O
• Canonical SMILES: 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@]1([C@@H]2O1)CC)C(=O)OC
• InChI: InChI=1S/C46H54N4O10/c1-7-42-15-11-17-49-19-16-44(37(42)49)30-20-31(34(56-4)21-33(30)50(25-51)38(44)46(55,41(54)58-6)39(42)59-26(3)52)45(40(53)57-5)22-27-23-48(24-43(8-2)36(27)60-43)18-14-29-28-12-9-10-13-32(28)47-35(29)45/h9-13,15,20-21,25,27,36-39,47,55H,7-8,14,16-19,22-24H2,1-6H3/t27-,36-,37+,38-,39-,42-,43+,44-,45+,46+/m1/s1
• InChIKey: GLDSBTCHEGZWCV-HLTPFJCJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-8-formyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^4,^1^2.0^5,^1^0.0^1^6,^1^8]icosa-4(12),5,7,9-tetraene-13-carboxylate
• IUPAC Traditional name: methyl (1S,13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-8-formyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^4,^1^2.0^5,^1^0.0^1^6,^1^8]icosa-4(12),5,7,9-tetraene-13-carboxylate
• Synonyms: (3'α,4'α)-4'-Deoxy-3',4'-epoxy-22-oxovincaleukoblastine; 22-Oxoleurosine; F-Leurosine; Formylleurosine; Leuroformine; N-Demethyl-N-formylleurosine; N-Formyl N-demethylleurosine; NSC 269419; Vinformide; Vincristine Impurity G; N-Formyl Leurosine (Vincristine Impurity G)

Database IDs

• CAS Number: 54022-49-0
• PubChem SID: 162263534
• PubChem CID: 320745

CALCULATED PROPERTIES

• Acid pKa: 10.847627
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -1.5909704
• LogD (pH = 7.4): 1.8922454
• Log P: 3.2565358
• Molar Refractivity: 219.233 cm^3
• Polarizability: 87.18555 Å^3
• Polar Surface Area: 163.47 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 200-210°C

Safety Information

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

DETAILS

Toronto Research Chemicals - F700650

Degradation products of Vincristine. A Vinca dimer, a potent cytostatic agent. Vincristine Impurity G.

REFERENCES

• Erdelyi-Toth, V., et al.: Eur. J. Cancer, 17, 329 (1981)
• Ronai-Lukacs S; Eur. J. Drug Metab. Pharmacokinet., 7, 4 (1981)