(2H3)methyl (1R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

• ChemBase ID: 163858
• Molecular Formular: C21H24N2O2
• Molecular Mass: 336.42746
• Monoisotopic Mass: 336.18377802
• SMILES: [C@]12([C@H]3C(=CC(C1)CN3CCc1c2[nH]c2c1cccc2)CC)C(=O)OC
• Canonical SMILES: CCC1=CC2CN3[C@H]1[C@@](C2)(C(=O)OC)c1[nH]c2c(c1CC3)cccc2
• InChI: InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13?,19-,21+/m1/s1
• InChIKey: CMKFQVZJOWHHDV-QYWJTTNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (^2H₃)methyl (1R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^2,^1^0.0^4,^9.0^1^3,^1^8]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• IUPAC Traditional name: (^2H₃)methyl (1R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^2,^1^0.0^4,^9.0^1^3,^1^8]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• Synonyms: (2α,5β,6α,18β)-3,4-Didehydro-ibogamine-18-carboxylic Acid Methyl-d3 Ester; (+)-3,4-Didehydrocoronaridine-d3; (+)-Catharanthine-d3; Catharanthin-d3; Catharanthine-d3

Database IDs

• CAS Number: 133146-02-8
• PubChem SID: 162257993
• PubChem CID: 46780197

CALCULATED PROPERTIES

• Acid pKa: 16.37115
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2133898
• LogD (pH = 7.4): 2.8449984
• Log P: 3.191243
• Molar Refractivity: 98.7115 cm^3
• Polarizability: 39.27758 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - C225402

Isotope labelled precursor of Vinblastine-type alkaloids.

REFERENCES

• Thomas, J., et al.: Plant TPhysiol., 109, 717 (1995)
• Contin, A., et al.: Plant Sci., 147, 177 (1995)
• Yalamanchili, R., et al.: J. Biol. Chem., 277, 28424 (1995)