sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,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]-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: 132435
• Molecular Formular: C46H60N4O13S
• Molecular Mass: 909.0526
• Monoisotopic Mass: 908.387759
• SMILES: CC[C@@]1(C[C@H]2C[C@@](c3c(c4ccccc4[nH]3)CCN(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)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
• InChI: InChI=1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1
• InChIKey: KDQAABAKXDWYSZ-PNYVAJAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,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]-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; sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,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]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate
• IUPAC Traditional name: sulfuric acid; vinblastine
• Synonyms: VLB; Vincaleukoblastine sulfate salt; Vinblastine sulfate salt

Database IDs

• CAS Number: 143-67-9
• EC Number: 205-606-0
• MDL Number: MFCD00082457
• Beilstein Number: 3659812
• PubChem SID: 162226712; 24278771
• PubChem CID: 5388983

CALCULATED PROPERTIES

• Acid pKa: 10.869524
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.6706752
• LogD (pH = 7.4): 1.8057727
• Log P: 4.1831455
• Molar Refractivity: 222.4206 cm^3
• Polarizability: 87.76486 Å^3
• Polar Surface Area: 154.1 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble50 mg/mL; H2O: soluble10 mg/mL
• Apperance: white powder
• Melting Point: 267 °C (dec.)(lit.)
• Absorption Wavelength: A1mM/214 nm, ethanol 53.7; A1mM/259 nm, ethanol 16.2; A1mM/270 nm, 0.1 M phosphate buffer 14

Safety Information

• RTECS: YY8400000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-36/39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TBCC(6903)

Product Information

• Purity: ≥96% (HPLC); ≥96.0% (TLC)
• Salt Data: H2SO4
• Impurities: ≤15% solvent (ethanol)
• Quality: crystallized
• Empirical Formula (Hill Notation): C46H58N4O9 · H2SO4
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - V1377

Biochem/physiol Actions
Plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing self-association in spiral aggregates in a reaction that appears to be regulated by the C-terminus of β-tubulin and is enhanced by GDP and GTP. Depolymerizes microtubules. Arrests the cell cycle in G2/M-phase by blocking mitotic spindle formation. Triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. Substrate of Pgp and CYP3A4.

Sigma Aldrich - 94897

Other Notes
Induces microtubule aggregation 1; Studies on Tau-tubulin-vinblastine aggregation 2; Inhibits monoamine oxidase B. 3