sulfuric acid methyl (13S,17S)-13-[(1R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

• ChemBase ID: 179520
• Molecular Formular: C43H57N5O11S
• Molecular Mass: 852.00458
• Monoisotopic Mass: 851.37752867
• SMILES: c1ccc2c(c1)c1c([nH]2)[C@](CC2CN(CC1)C[C@](C2)(O)CC)(c1c(cc2c(c1)[C@]13C(N2C)[C@]([C@@H]([C@]2([C@@H]3N(CC1)CC=C2)CC)O)(C(=O)N)O)OC)C(=O)OC.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.COc1cc2N(C)C3[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)N)O)(CC)C=CC1
• InChI: InChI=1S/C43H55N5O7.H2O4S/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50;1-5(2,3)4/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50);(H2,1,2,3,4)/t25?,34-,35?,36+,39-,40+,41+,42-,43-;/m0./s1
• InChIKey: COFJBSXICYYSKG-NLWKUBGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (13S,17S)-13-[(1R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-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-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
• IUPAC Traditional name: sulfuric acid methyl (13S,17S)-13-[(1R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-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-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
• Synonyms: LY-099094; Eldisine; Fildesin; Vindesine Sulfate Salt

Database IDs

• CAS Number: 59917-39-4
• PubChem SID: 164235430
• PubChem CID: 57369774

CALCULATED PROPERTIES

• Acid pKa: 11.342998
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.6965613
• LogD (pH = 7.4): 0.8213256
• Log P: 2.7891831
• Molar Refractivity: 210.3222 cm^3
• Polarizability: 82.5302 Å^3
• Polar Surface Area: 164.82 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: >250°C

Safety Information

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

DETAILS

Toronto Research Chemicals - V414550

Synthetic derivative of the dimeric Catharanthus alkaloid vinblastine. Antineoplastic.

REFERENCES

• Todd, G.C., et al.: Toxicol. Environ. Health 1, 843 (1976)
• Owellen, J.R., et al.: Biochem. Pharmacol., 26, 1213 (1976)