(3R)-3-[(3-methylbut-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoate

• ChemBase ID: 173467
• Molecular Formular: C12H21NO4
• Molecular Mass: 243.29944
• Monoisotopic Mass: 243.14705816
• SMILES: C([C@H](C[N+](C)(C)C)OC(=O)C=C(C)C)C(=O)[O-]
• Canonical SMILES: [O-]C(=O)C[C@H](C[N+](C)(C)C)OC(=O)C=C(C)C
• InChI: InChI=1S/C12H21NO4/c1-9(2)6-12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3/t10-/m1/s1
• InChIKey: KGPNNIOVWVIXOR-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(3-methylbut-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoate
• IUPAC Traditional name: (3R)-3-[(3-methylbut-2-enoyl)oxy]-4-(trimethylammonio)butanoate
• Synonyms: (2R)-3-Carboxy-N,N,N-trimethyl-2-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-1-propanaminium Inner Salt; 3-Methylcrotonyl L-Carnitine

Database IDs

• CAS Number: 64656-41-3
• PubChem SID: 164229377
• PubChem CID: 71750254

CALCULATED PROPERTIES

• Acid pKa: 4.2951403
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -2.077939
• LogD (pH = 7.4): -2.0565088
• Log P: -2.8267581
• Molar Refractivity: 87.24 cm^3
• Polarizability: 25.256876 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M294535

A metabolite of L-Carnitine (C184110).

REFERENCES

• Millington, D., et al.: J. Inherit. Metab. Dis., 13, 321 (1990)
• Chace, D., et al.: Clin. Chem., 49, 1797 (1990)