(3R)-3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate

• ChemBase ID: 178268
• Molecular Formular: C21H39NO4
• Molecular Mass: 369.53866
• Monoisotopic Mass: 369.28790873
• SMILES: C([C@@H](OC(=O)CCC/C=C\CCCCCCCC)C[N+](C)(C)C)C(=O)[O-]
• Canonical SMILES: CCCCCCCC/C=C\CCCC(=O)O[C@@H](C[N+](C)(C)C)CC(=O)[O-]
• InChI: InChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3/b13-12-/t19-/m1/s1
• InChIKey: NNCBVXBBLABOCB-SYGIOELKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate
• IUPAC Traditional name: (3R)-3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylammonio)butanoate
• Synonyms: (2R)-3-carboxy-N,N,N-trimethyl-2-[[(5Z)-1-oxo-5-tetradecen-1-yl]oxy]-1-propanaminium Inner Salt; 5-cis-Tetradecenoyl Carnitine

Database IDs

• CAS Number: 1186416-86-3
• PubChem SID: 164234178
• PubChem CID: 71752411

CALCULATED PROPERTIES

• Acid pKa: 4.235691
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.5340009
• LogD (pH = 7.4): 1.5527743
• Log P: 0.7824889
• Molar Refractivity: 128.9913 cm^3
• Polarizability: 41.793808 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T291425

One of the metabolites found in the lymph fluid collected from dietary stressed rats.

REFERENCES

• Ardawi, M., et al.: Biochem. J., 212, 835 (1983)
• Otton, R., et al.: J. Endocrinol., 174, 55 (1983)
• Gu, H., et al.: Anal. Chem., 79, 89 (1983)