4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-hydroxybenzamide

• ChemBase ID: 166487
• Molecular Formular: C22H27ClFN3O4
• Molecular Mass: 451.9188832
• Monoisotopic Mass: 451.16741226
• SMILES: c1cc(ccc1OCCCN1C[C@H]([C@@H](CC1)NC(=O)c1c(cc(c(c1)Cl)N)O)OC)F
• Canonical SMILES: CO[C@@H]1CN(CCCOc2ccc(cc2)F)CC[C@H]1NC(=O)c1cc(Cl)c(cc1O)N
• InChI: InChI=1S/C22H27ClFN3O4/c1-30-21-13-27(8-2-10-31-15-5-3-14(24)4-6-15)9-7-19(21)26-22(29)16-11-17(23)18(25)12-20(16)28/h3-6,11-12,19,21,28H,2,7-10,13,25H2,1H3,(H,26,29)/t19-,21-/m1/s1
• InChIKey: WUYNAGSDZADZCE-TZIWHRDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-hydroxybenzamide
• IUPAC Traditional name: 4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-hydroxybenzamide
• Synonyms: cis-4-Amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-hydroxy-benzamide; rel-4-Amino-5-chloro-N-[1-[(3R,4S)-3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-hydroxybenzamide; 2-O-Desmethyl Acenalin; 2-O-Desmethyl Alimix; 2-O-Desmethyl Cipril; 2-O-Desmethyl Coordinax; 2-O-Desmethyl Prepulsid; 2-O-Desmethyl Propulsid; 2-O-Desmethyl Propulsin; 2-O-Desmethyl Cisapride

Database IDs

• CAS Number: 102671-04-5
• PubChem SID: 162260620
• PubChem CID: 71315756

CALCULATED PROPERTIES

• Acid pKa: 7.6660023
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.3650638
• LogD (pH = 7.4): 2.0051537
• Log P: 2.2101321
• Molar Refractivity: 118.4526 cm^3
• Polarizability: 44.85295 Å^3
• Polar Surface Area: 97.05 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dimethylformamide; DMSO; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - D291985

Minor Cisapride (C496400) metabolite.

REFERENCES

• Meuldermans, W., et al.; Drug Metab. Disposition, 16, 410 (1988)
• Lowry J., et al.; Clin. pharmacol. ther., 73, 209 (1988)
• Shao L., et al.: Bioorg. Med. Chem. Lett., 19, 5679 (1988)