(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-carboxylic acid

• ChemBase ID: 160766
• Molecular Formular: C20H22N2O2
• Molecular Mass: 322.40088
• Monoisotopic Mass: 322.16812795
• SMILES: c1ccc2c(c1)n1c3c2CCN2[C@H]3[C@@](C=C1C(=O)O)(CCC2)CC
• Canonical SMILES: CC[C@@]12CCCN3[C@@H]2c2n(C(=C1)C(=O)O)c1c(c2CC3)cccc1
• InChI: InChI=1S/C20H22N2O2/c1-2-20-9-5-10-21-11-8-14-13-6-3-4-7-15(13)22(17(14)18(20)21)16(12-20)19(23)24/h3-4,6-7,12,18H,2,5,8-11H2,1H3,(H,23,24)/t18-,20-/m1/s1
• InChIKey: ZFCQLDAGNBFMJQ-UYAOXDASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-carboxylic acid
• IUPAC Traditional name: (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-carboxylic acid
• Synonyms: (13aS,13bS)-13a-Ethyl-2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylic Acid-d4; Apovincamin-22-oic Acid-d4; (3α,16α)-Eburnamenine-14-carboxylic Acid-d4; (+)-Apovincaminic Acid-d4; (+)-cis-Apovincaminic Acid-d4; Apovincaminic Acid-d4

Database IDs

• PubChem SID: 162254901
• PubChem CID: 71313472

CALCULATED PROPERTIES

• Acid pKa: 4.0103145
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.70541185
• LogD (pH = 7.4): 0.4528504
• Log P: 0.7024369
• Molar Refractivity: 94.7207 cm^3
• Polarizability: 37.2645 Å^3
• Polar Surface Area: 45.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A729252

The main labelled metabolite of Vinpocetine (V332502), a vasodilator cerebral.

REFERENCES

• Miskolczi, P., et al.: Eur. J. Clin. Pharmacol., 33, 185 (1987)
• Kiss, B., et al.: Eur. J. Pharmacol., 209, 109 (1987)
• Stephenson, D., et al.: J. Neurosci., 15, 5263 (1987)