(3S)-3-amino-4-(trimethylazaniumyl)butanoate

• ChemBase ID: 159921
• Molecular Formular: C7H16N2O2
• Molecular Mass: 160.21414
• Monoisotopic Mass: 160.12117776
• SMILES: [N+](C[C@H](CC(=O)[O-])N)(C)(C)C
• Canonical SMILES: N[C@H](C[N+](C)(C)C)CC(=O)[O-]
• InChI: InChI=1S/C7H16N2O2/c1-9(2,3)5-6(8)4-7(10)11/h6H,4-5,8H2,1-3H3/t6-/m0/s1
• InChIKey: DAWBGYHPBBDHMQ-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-4-(trimethylazaniumyl)butanoate
• IUPAC Traditional name: (3S)-3-amino-4-(trimethylammonio)butanoate
• Synonyms: (2S)-2-Amino-3-carboxy-N,N,N-trimethyl-1-propanaminium Inner Salt; (S)-3-Amino-4-(trimethylammonio)butyrate; (S)-Emeriamine; (S)-Amino Carnitine

Database IDs

• CAS Number: 125377-87-9
• PubChem SID: 162254056
• PubChem CID: 10197827

CALCULATED PROPERTIES

• Acid pKa: 3.8351104
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -6.813661
• LogD (pH = 7.4): -5.148007
• Log P: -6.4310865
• Molar Refractivity: 65.1428 cm^3
• Polarizability: 17.03152 Å^3
• Polar Surface Area: 66.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A603405

An inhibitor of fatty acid oxidation. Aminocarnitine acts as a hypoglycemic and antiketogenic compound. It alters lipidic metabolism by inhibiting carnitine acetyltransferase (CAT) and carnitine palmitoyltransferase (CPT).

REFERENCES

• Jenkins, D.L., et al.: J. Biol. Chem., 260, 14748 (1985)
• Kanamaru, T., et al.: M. Life Sci., 37, 217 (1985)
• Hulsmann, W.C., et al.: J. Biochim. Biophys. Acta., 1097, 263 (1985)
• Chiodi, P., et al.: Biochim, Biophys. Acta., 1127, 81 (1985)