3-(3S)-1-benzyl(2,2,5,5-2H4)pyrrolidin-3-yl 5-methyl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

• ChemBase ID: 161115
• Molecular Formular: C27H30ClN3O6
• Molecular Mass: 527.9966
• Monoisotopic Mass: 527.18231338
• SMILES: C1C[C@@H](CN1Cc1ccccc1)OC(=O)C1=C(NC(=C([C@@H]1c1cccc(c1)[N+](=O)[O-])C(=O)OC)C)C.Cl
• Canonical SMILES: COC(=O)C1=C(C)NC(=C([C@H]1c1cccc(c1)[N+](=O)[O-])C(=O)O[C@H]1CCN(C1)Cc1ccccc1)C.Cl
• InChI: InChI=1S/C27H29N3O6.ClH/c1-17-23(26(31)35-3)25(20-10-7-11-21(14-20)30(33)34)24(18(2)28-17)27(32)36-22-12-13-29(16-22)15-19-8-5-4-6-9-19;/h4-11,14,22,25,28H,12-13,15-16H2,1-3H3;1H/t22-,25-;/m0./s1
• InChIKey: XEMPUKIZUCIZEY-YSCHMLPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3S)-1-benzyl(2,2,5,5-^2H₄)pyrrolidin-3-yl 5-methyl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• IUPAC Traditional name: 3-(3S)-1-benzyl(2,2,5,5-^2H₄)pyrrolidin-3-yl 5-methyl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• Synonyms: (4S)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-Pyridinedicarboxylic Acid 3-Methyl 5-[(3S)-1-(phenylmethyl)-3-(pyrrolidinyl-d4)] Ester Hydrochloride; [S-(R*,R*)]-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 1-(Phenylmethyl)-3-(pyrrolidinyl-d4) Ester Monohydrochloride; YM 09730-5; Barnidipine-d4 Hydrochloride

Database IDs

• PubChem SID: 162255250
• PubChem CID: 13631677

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.6156461
• LogD (pH = 7.4): 2.6457567
• Log P: 3.5068138
• Molar Refractivity: 137.363 cm^3
• Polarizability: 51.668053 Å^3
• Polar Surface Area: 113.69 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B118702

Labelled 1,4-dihydropyridine calcium antagonist with antihypertensive and diuretic effects. A potential candidate in the treatment of patients with renal parenchymal hypertension.

REFERENCES

• Ohya, Y. et al.: Int. J. Clin. Pharmacol. Therap., 38, 304 (2000)
• Huh, W. S. et al.: Curr. Therap. Res., 61, 395 (2000)
• Katoh, M. et al.: Eur. J. Clin. Pharmacol., 55, 843 (2000)