methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-10,11-dihydroxy-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: 166135
• Molecular Formular: C23H30N2O5
• Molecular Mass: 414.4947
• Monoisotopic Mass: 414.21547207
• SMILES: [C@]123[C@H]([C@]([C@@H]([C@]4([C@@H]1N(CC=C4)CC3)CC)O)(C(=O)OC)O)N(c1c2ccc(c1)OC)C
• Canonical SMILES: COc1ccc2c(c1)N(C)[C@@H]1[C@@]32CCN2[C@H]3[C@@]([C@H]([C@]1(O)C(=O)OC)O)(CC)C=CC2
• InChI: InChI=1S/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/t17-,18+,19+,21+,22+,23-/m0/s1
• InChIKey: ZDKMPOJNYNVYLA-PEGGBQQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-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(7),3,5,13-tetraene-10-carboxylate
• IUPAC Traditional name: methyl (1R,9R,10S,11R,12R,19R)-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(7),3,5,13-tetraene-10-carboxylate
• Synonyms: (2β,3β,4β,5α,12R,19α)-6,7-Didehydro-3,4-dihydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic Acid Methyl Ester; 4-Desacetylvindoline; Deacetylvindoline; NSC 91993; Desacetyl Vindoline

Database IDs

• CAS Number: 3633-92-9
• PubChem SID: 162260268
• PubChem CID: 260534

CALCULATED PROPERTIES

• Acid pKa: 10.898378
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.4082592
• LogD (pH = 7.4): 0.34781042
• Log P: 1.441512
• Molar Refractivity: 113.1466 cm^3
• Polarizability: 43.844093 Å^3
• Polar Surface Area: 82.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D288745

Precursor to Vindoline during Vincristine biosynthesis.

REFERENCES

• Bornmann, W., et al.: Biochem., 33, 12665 (1994)
• Passarella, D., et al.: Bioorg. Med. Chem., 16, 6269 (1994)
• Levac, D., et al.: Plant J., 53, 225 (1994)