2,3-dihydroxybutanedioic acid methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

• ChemBase ID: 167742
• Molecular Formular: C49H62N4O14
• Molecular Mass: 931.03498
• Monoisotopic Mass: 930.42625268
• SMILES: c1cc2c(cc1)c1c([nH]2)[C@@](C[C@H]2CN(C1)CC(C2)CC)(C(=O)OC)c1cc2[C@@]34[C@H]([C@@]([C@H]([C@]5([C@@H]3N(CC=C5)CC4)CC)OC(=O)C)(O)C(=O)OC)N(c2cc1OC)C.C(C(O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)C(C(C(=O)O)O)O.CCC1CN2C[C@@H](C1)C[C@](c1c(C2)c2ccccc2[nH]1)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@@H]([C@]1(O)C(=O)OC)OC(=O)C)C
• InChI: InChI=1S/C45H56N4O8.C4H6O6/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7;5-1(3(7)8)2(6)4(9)10/h10-15,20-21,27-28,37-39,46,53H,8-9,16-19,22-25H2,1-7H3;1-2,5-6H,(H,7,8)(H,9,10)/t27?,28?,37-,38+,39-,42+,43+,44-,45-;/m0./s1
• InChIKey: OXIMHTGYMDJCKQ-KKXWJQDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8-tetraen-12-yl]-10-hydroxy-5-methoxy-8-methyl-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: (.+-.)-tartaric acid methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1S,12S,14S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8-tetraen-12-yl]-10-hydroxy-5-methoxy-8-methyl-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-15-[(2S,4RS,6S,8S)-4-ethyl-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid Methyl Ester Ditartarate; (20'RS)-15',20'-Dihydro Vinorelbine Ditartarate

Database IDs

• PubChem SID: 162261875
• PubChem CID: 71316208

CALCULATED PROPERTIES

• Acid pKa: 10.870628
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.004228
• LogD (pH = 7.4): 2.4309683
• Log P: 4.97583
• Molar Refractivity: 216.2145 cm^3
• Polarizability: 85.37133 Å^3
• Polar Surface Area: 133.87 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D450020

A dihydro derivative of the antineoplastic Vinorelbine Ditartarate (V315000). Studies show that its vinca-induced tubulin-spiraling potential is significantly correlated with cytotoxicity against L1210 cells.

REFERENCES

• Lobert, S. et al.: Biochemistry, 39, 12053 (2000)
• Jacquesy, J.: J. Fluor. Chem., 127, 1484 (2000)