3-(3S)-1-benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

• ChemBase ID: 165611
• Molecular Formular: C27H27N3O6
• Molecular Mass: 489.51978
• Monoisotopic Mass: 489.1899856
• SMILES: C1C[C@@H](CN1Cc1ccccc1)OC(=O)c1c(c(C(=O)OC)c(nc1C)C)c1cccc(c1)[N+](=O)[O-]
• Canonical SMILES: COC(=O)c1c(C)nc(c(c1c1cccc(c1)[N+](=O)[O-])C(=O)O[C@H]1CCN(C1)Cc1ccccc1)C
• InChI: InChI=1S/C27H27N3O6/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/h4-11,14,22H,12-13,15-16H2,1-3H3/t22-/m0/s1
• InChIKey: DFWOMDUVXAUTRY-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3S)-1-benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
• IUPAC Traditional name: 3-(3S)-1-benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
• Synonyms: Methyl 2,6-Dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid (3S)-1-(Phenylmethyl)-3-pyrrolidinyl Ester; Dehydro Barnidipine

Database IDs

• CAS Number: 172331-68-9
• PubChem SID: 162259744
• PubChem CID: 71315296

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.7705783
• LogD (pH = 7.4): 3.5576942
• Log P: 4.303797
• Molar Refractivity: 134.7939 cm^3
• Polarizability: 52.377716 Å^3
• Polar Surface Area: 114.55 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229290

A metabolite of Barnidipine (B118700) in human plasma.

REFERENCES

• Tamazawa, K., et al.: J. Med. Chem., 29, 2504 (1986)
• Shimooka, K., et al.: J. Pharm. Biomed. Anal., 7, 638 (1986)
• Teramura, T., et al.: Xenobiotica, 27, 203 (1997)