ethyl (15R,19S)-15-ethyl(3,4,5,6-2H4)-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate

• ChemBase ID: 179517
• Molecular Formular: C22H26N2O2
• Molecular Mass: 350.45404
• Monoisotopic Mass: 350.19942808
• SMILES: c1ccc2c(c1)n1c3c2CCN2[C@H]3[C@@](C=C1C(=O)OCC)(CCC2)CC
• Canonical SMILES: CCOC(=O)C1=C[C@@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
• InChI: InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22-/m1/s1
• InChIKey: DDNCQMVWWZOMLN-IFMALSPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (15R,19S)-15-ethyl(3,4,5,6-^2H₄)-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
• IUPAC Traditional name: ethyl (15R,19S)-15-ethyl(3,4,5,6-^2H₄)-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
• Synonyms: (3α,16α)-Eburnamenine-14-carboxylic-d4 Acid Ethyl Ester; (+)-Apovincaminic Acid-d4 Ethyl Ester; (+)-Vinpocetine-d4; (+)-cis-Apovincaminic Acid-d4 Ethyl Ester; AY 27255-d4; Apovincaminic Acid-d4 Ethyl Ester; Bravinton-d4; Cavinton-d4; Ceractin-d4; Ethyl (+)-Apovincaminate-d4; Ethyl (+)-cis-Apovincaminate-d4; Ethyl Apovincaminate-d4; RGH 4405-d4; TCV 3B-d4; Ultra-Vinca-d4; Vinporal-d4; cis-Apovincaminic Acid-d4 Ethyl Ester; Vinpocetine-d4

Database IDs

• PubChem SID: 164235427
• PubChem CID: 71752964

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.3386369
• LogD (pH = 7.4): 3.843793
• Log P: 4.0670204
• Molar Refractivity: 104.2384 cm^3
• Polarizability: 41.217064 Å^3
• Polar Surface Area: 34.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V332502

A labelled derivative of Vincamine with vasodilating activity. Vasodilator (cerebral).

REFERENCES

• Han, et al.: J. Biol. Chem., 274, 22337 (1999)
• O’Donnell, et al.: Pharmacol. Biochem. Behav., 63, 185 (1999)