2-[(4-amino-5-chloro-2-methoxyphenyl)formamido]acetic acid

• ChemBase ID: 166198
• Molecular Formular: C10H11ClN2O4
• Molecular Mass: 258.65834
• Monoisotopic Mass: 258.04073452
• SMILES: c1(c(cc(c(c1)C(=O)NCC(=O)O)OC)N)Cl
• Canonical SMILES: COc1cc(N)c(cc1C(=O)NCC(=O)O)Cl
• InChI: InChI=1S/C10H11ClN2O4/c1-17-8-3-7(12)6(11)2-5(8)10(16)13-4-9(14)15/h2-3H,4,12H2,1H3,(H,13,16)(H,14,15)
• InChIKey: LNQXFAOBVQSPCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-amino-5-chloro-2-methoxyphenyl)formamido]acetic acid
• IUPAC Traditional name: [(4-amino-5-chloro-2-methoxyphenyl)formamido]acetic acid
• Synonyms: N-(4-Amino-5-chloro-2-methoxybenzoyl)glycine; 2-[4-Amino-5-chloro-2-methoxybenzoyl)amino]acetic Acid; N-Des(2-diethylamino) Metoclopramide Acetic Acid

Database IDs

• CAS Number: 65567-29-5
• PubChem SID: 162260331
• PubChem CID: 15188246

CALCULATED PROPERTIES

• Acid pKa: 3.28941
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.0821092
• LogD (pH = 7.4): -3.2921424
• Log P: -0.035652902
• Molar Refractivity: 62.0861 cm^3
• Polarizability: 23.082947 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289015

The only common metabolite of Metoclopramide (M338685) in rat, dog and human; an oxidative deaminated metabolite.

REFERENCES

• Bateman, D., et al.: Clin. Pharmacokinet., 8, 523 (1983)
• Vlase, L., et al.: Biopharm. Drug Dispos., 27, 285 (1983)
• Gunduz, M., et al.: Drug Metab. Dispos., 38, 361 (1983)