(3R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate

• ChemBase ID: 172335
• Molecular Formular: C25H45NO4
• Molecular Mass: 423.6291
• Monoisotopic Mass: 423.33485893
• SMILES: [N+](C[C@@H](CC(=O)[O-])OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)(C)(C)C
• Canonical SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@@H](C[N+](C)(C)C)CC(=O)[O-]
• InChI: InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/b10-9-,13-12-/t23-/m1/s1
• InChIKey: MJLXQSQYKZWZCB-DQFWFXSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate
• IUPAC Traditional name: linoleoylcarnitine
• Synonyms: (2R)-3-Carboxy-N,N,N-trimethyl-2-[[(9Z,12Z)-1-oxo-9,12-octadecadien-1-yl]oxy]-1-propanaminium Inner Salt; L-Linoleoylcarnitine; Linoleoylcarnitine; Linoleoyl Carnitine

Database IDs

• CAS Number: 36816-10-1
• PubChem SID: 164228245
• PubChem CID: 6450015

CALCULATED PROPERTIES

• Acid pKa: 4.216764
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.9511414
• LogD (pH = 7.4): 2.969138
• Log P: 2.1988418
• Molar Refractivity: 148.5119 cm^3
• Polarizability: 48.920036 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L468200

A carnitine ester of unsaturated fatty acid. Used in the studies of fibroblasts in long-chain 3-hydroxyacyl-CoA dehydrogenase deficiency and fatty acid oxidation disorders.

REFERENCES

• Gross R.W., et al.: J. Biol. Chem., 258, 5221 (1983)