2-[2-amino-6-(2-{bis[(1,1-2H2)propyl]amino}ethyl)phenyl]acetic acid

• ChemBase ID: 177597
• Molecular Formular: C16H26N2O2
• Molecular Mass: 278.38984
• Monoisotopic Mass: 278.19942808
• SMILES: c1cc(c(c(c1)N)CC(=O)O)CCN(CCC)CCC
• Canonical SMILES: CCCN(CCc1cccc(c1CC(=O)O)N)CCC
• InChI: InChI=1S/C16H26N2O2/c1-3-9-18(10-4-2)11-8-13-6-5-7-15(17)14(13)12-16(19)20/h5-7H,3-4,8-12,17H2,1-2H3,(H,19,20)
• InChIKey: XGMMSJHVWLZZPC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-amino-6-(2-{bis[(1,1-^2H₂)propyl]amino}ethyl)phenyl]acetic acid
• IUPAC Traditional name: (2-amino-6-{2-[bis(1,1-^2H₂)propylamino]ethyl}phenyl)acetic acid
• Synonyms: 2-Amino-6-[2-(dipropylamino-d4)ethyl]benzeneacetic Acid Dihydrochloride; Ropinirole Aminoacetic Acid-d4 Dihydrochloride

Database IDs

• PubChem SID: 164233507
• PubChem CID: 71752105

CALCULATED PROPERTIES

• Acid pKa: 4.5423717
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -6.008779E-4
• LogD (pH = 7.4): 0.039222196
• Log P: 0.038641244
• Molar Refractivity: 83.9089 cm^3
• Polarizability: 31.839823 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R641017

Labelled Ropinirole (R641000) impurity. It was found that these compounds were all poor competitive inhibitors of GABA-AT, but some were substrates of the enzyme, suggesting their utility as scaffolds for potential GABA-AT mechanism-based inactivators.

REFERENCES

• Karlsson, A., et al.: J. Biochem. Pharmacol., 23, 3053 (1974)
• Hayashi, T., J. Med. Chem., 24, 1377 (1974)