methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

• ChemBase ID: 109739
• Molecular Formular: C21H24N2O3
• Molecular Mass: 352.42686
• Monoisotopic Mass: 352.17869264
• SMILES: COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCc4c([nH]c5c4cccc5)[C@@H]3C[C@H]12
• Canonical SMILES: COC(=O)C1=CO[C@H]([C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1)C
• InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1
• InChIKey: GRTOGORTSDXSFK-XJTZBENFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate; methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• IUPAC Traditional name: substance II; methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• Synonyms: AJMALICINE; (19α)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic Acid Methyl Ester; (-)-Ajmalicine; Ajmalicin; Circolene; Hydrosarpan; Isoarteril; Lamuran; Ranitol; Raubaserp; Raubasil; Raubasin; Raumalina; Rauvasan; Sarpan; Tensyl; Tetrahydroserpentine; Vincain; Vincaine; Vincein; Vinceine; δ-Yohimbine; NSC 72133; NSC 95087; Raubasine; Raubasine; Delta-Yohimbine; Py-tetrahydroserpentine; Ajmalicine

Database IDs

• CAS Number: 483-04-5
• PubChem SID: 162095386
• PubChem CID: 441975

CALCULATED PROPERTIES

• Acid pKa: 16.374712
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.4513834
• LogD (pH = 7.4): 2.1309202
• Log P: 2.5527265
• Molar Refractivity: 99.8364 cm^3
• Polarizability: 39.949436 Å^3
• Polar Surface Area: 54.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Cryst.

Pharmacology Properties

• Mechanism of Action: CYP2D6 inhibitor; Vasodilator

Product Information

• Biological Source: Alkaloid from Alstonia, Amsonia, Cabucala, Catharanthus, Mitragyna, Rauwolfia, Uncaria and Voacanga spp. (Apocynaceae, Naucleaceae)
• Application(s): Antidiuretic agent; CNS depressant; Has been used to treat peripheral and cerebral vascular disorders; Vasodilator

DETAILS

MP Biomedicals - 05212392

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - R127000

Antihypertensive, anti-ischemic.

REFERENCES

• Caillet, S., et al.: Food Chem., 124, 1699 (2010)
• Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2010)
• Ferreres, F., et al.: J. Pharm. Biomed. Anal., 51, 65 (2010)
• Klohs, M.W. et al., J.A.C.S., 1954, 76, 1332, (isol, uv, ir)
• Antonaccio, L.D. et al., J.A.C.S., 1962, 84, 2161, (ms)
• Shamma, M. et al., J.A.C.S., 1963, 85, 2507, (ir, pmr, config)
• Laubie, M. et al., Arzneim.-Forsch., 1969, 19, 1820, (pharmacol)
• van Tamelen, E.E. et al., J.A.C.S., 1969, 91, 7359, (synth)
• Gutzwiller, J. et al., J.A.C.S., 1971, 93, 5907, (synth, ir, ms, pmr)
• Levin, R.H. et al., J.O.C., 1973, 38, 1983, (cmr)
• Lohr, J.P. et al., Arzneim.-Forsch., 1975, 25, 870, (metab)
• Brown, R.T. et al., Chem. Comm., 1977, 636, (synth)
• Hernandez, N.M.R. et al., Rev. Cubana Farm., 1977, 11, 249-255, (activity)
• Stckigt, J., Phytochemistry, 1979, 18, 965, (biosynth)
• Gutzwiller, J. et al., Helv. Chim. Acta, 1981, 64, 1663, (synth)
• Wenkert, E. et al., Acta Chem. Scand., Ser. B, 1982, 36, 607, (stereochem, configuration)
• Seguin, E. et al., Helv. Chim. Acta, 1983, 66, 2059, (cd)
• Massiot, G. et al., Chem. Comm., 1984, 715, (synth)
• Lala, P.K., J. Inst. Chem. (India), 1984, 56, 42, (ms)
• Hatakeyama, S. et al., Tet. Lett., 1985, 26, 865, (synth)
• Naito, T. et al., Heterocycles, 1986, 24, 2117, (synth)
• Mekkawi, A.G. et al., Anal. Profiles Drug Subst., 1987, 16, 731, (rev)
• Morales-Rios, M.S. et al., Magn. Reson. Chem., 1987, 25, 377, (cmr)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6133
• Takano, S. et al., Chem. Comm., 1988, 59, (synth)
• Hirai, Y. et al., J.A.C.S., 1988, 110, 958, (synth)
• Hanessian, S. et al., J.O.C., 1991, 56, 2947, (synth)
• Honda, T. et al., J.C.S. Perkin 1, 1993, 539
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 9277
• Lgers, M. et al., J.A.C.S., 1995, 117, 9139, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AFG750