sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0?,??.0?,??]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0?,?.0?,?.0??,??]nonadeca-2,4,6,13-tetraene-10-carboxylate

• ChemBase ID: 105461
• Molecular Formular: C46H60N4O13S
• Molecular Mass: 909.0526
• Monoisotopic Mass: 908.387759
• SMILES: CC[C@@]1(CC2C[C@](c3cc4c(cc3OC)N(C)[C@@H]3[C@@]54CCN4CC=C[C@](CC)([C@@H]54)[C@H]([C@@]3(C(=O)OC)O)OC(=O)C)(c3c(CCN(C2)C1)c1ccccc1[nH]3)C(=O)OC)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(CC2CN(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-FCIBFBFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0?,??.0?,??]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0?,?.0?,?.0??,??]nonadeca-2,4,6,13-tetraene-10-carboxylate
• IUPAC Traditional name: sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0?,??.0?,??]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0?,?.0?,?.0??,??]nonadeca-2,4,6,13-tetraene-10-carboxylate
• Synonyms: VINBLASTINE SULFATE

Database IDs

• CAS Number: 143-67-9
• EC Number: 205-606-0
• PubChem SID: 162092408
• PubChem CID: 9962911

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

• Melting Point: 267°C

Safety Information

• Storage Condition: 2-8°C
• RTECS: YY8400000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:22
• Safety Statements: S:36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

DETAILS

MP Biomedicals - 02190287

Crystalline
An anti-tumor alkaloid useful in cancer research.

REFERENCES

• Biochemistry, 18: 3760, (1979).