bis((2R,3R)-2,3-dihydroxybutanedioic acid) hydrate methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-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: 154137
• Molecular Formular: C53H68N4O21
• Molecular Mass: 1097.12122
• Monoisotopic Mass: 1096.43760522
• SMILES: CCC1=C[C@@H]2C[C@@](c3c(c4ccccc4[nH]3)CN(C2)C1)(c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](C=CC2)([C@H]([C@@]1(C(=O)OC)O)OC(=O)C)CC)C)C(=O)OC.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O.O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.OC(=O)[C@@H]([C@H](C(=O)O)O)O.CCC1=C[C@H]2CN(C1)Cc1c3ccccc3[nH]c1[C@@](C2)(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.O
• InChI: InChI=1S/C45H54N4O8.2C4H6O6.H2O/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;2*5-1(3(7)8)2(6)4(9)10;/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10);1H2/t28-,37-,38+,39+,42+,43+,44-,45-;2*1-,2-;/m011./s1
• InChIKey: ZLIPKSVXTCRHIB-GNBHHJMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((2R,3R)-2,3-dihydroxybutanedioic acid) hydrate methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8,15-pentaen-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: bis(L(+)-tartaric acid) vinorelbine hydrate
• Synonyms: 3′,4′-Didehydro-4′-deoxy-C′-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt]; 5′-Noranhydrovinoblastine tartrate; KW-2307; NVB; Navelbine tartrate; Vinorelbine ditartrate salt hydrate

Database IDs

• CAS Number: 125317-39-7(anhydrous)
• MDL Number: MFCD03613607
• PubChem SID: 162248276; 24724660
• PubChem CID: 16079018

CALCULATED PROPERTIES

• Acid pKa: 10.868411
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.86895776
• LogD (pH = 7.4): 2.6344895
• Log P: 4.6482043
• Molar Refractivity: 216.9875 cm^3
• Polarizability: 85.129105 Å^3
• Polar Surface Area: 133.87 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C45H54N4O8 · 2C4H6O6 · xH2O

DETAILS

Sigma Aldrich - V2264

Biochem/physiol Actions
Vinorelbine is a potent anti-mitotic, anti-tumor agent. Vinorelbine inhibits microtubule assembly. Low neurotoxicity is related to its higher affinity for mitotic microtubules than for axonal microtubules.