(15S,19S)-15-ethyl-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: 160765
• Molecular Formular: C20H22N2O2
• Molecular Mass: 322.40088
• Monoisotopic Mass: 322.16812795
• SMILES: c1ccc2c(c1)c1c3n2C(=C[C@]2([C@@H]3N(CC1)CCC2)CC)C(=O)O
• 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-QUCCMNQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (15S,19S)-15-ethyl-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: (15S,19S)-15-ethyl-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; Apovincamin-22-oic Acid; (3α,16α)-Eburnamenine-14-carboxylic Acid; (+)-Apovincaminic Acid; (+)-cis-Apovincaminic Acid; Apovincaminic Acid

Database IDs

• CAS Number: 27773-65-5
• PubChem SID: 162254900
• PubChem CID: 160154

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: 37.24595 Å^3
• Polar Surface Area: 45.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A729250

The main 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)