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Identification
YMDB IDYMDB00351
NameL-Acetylcarnitine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Acetylcarnitine, also known as alcar or branigen, belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, L-acetylcarnitine is considered to be a fatty ester lipid molecule. L-Acetylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (-)-Acetylcarnitine
  • (+-)-Acetylcarnitine
  • (R)-Acetylcarnitine
  • Acetyl-L-(-)-carnitine
  • Acetyl-L-carnitine
  • Acetylcarnitine
  • ALCAR
  • L-Acetylcarnitine
  • L-Carnitine acetyl ester
  • L-O-Acetylcarnitine
  • Levocarnitine acetyl
  • Nicetile
  • O-Acetyl-L-carnitine
  • O-Acetylcarnitine
  • O-Acetyl-(R)-carnitine
  • R-Acetylcarnitine
  • Branigen
  • Acetyl carnitine
  • Carnitine, acetyl
  • Acetyl L carnitine
  • Acetylcarnitine, (R)-isomer
  • Medosan
  • ALC
  • 3-(Acetyloxy)-4-(trimethylammonio)butanoate
  • Acetyl-DL-carnitine
  • DL-O-Acetylcarnitine
  • 3-(Acetyloxy)-4-(trimethylammonio)butanoic acid
  • Acetyl-carnitine
CAS number3040-38-8
WeightAverage: 203.2356
Monoisotopic: 203.115758037
InChI KeyRDHQFKQIGNGIED-UHFFFAOYSA-N
InChIInChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3
IUPAC Name(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Nameacetyl-L-carnitine
Chemical FormulaC9H17NO4
SMILES[H]C([H])([H])C(=O)OC([H])(C([H])([H])C([O-])=O)C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point145 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP-2.4ALOGPS
logP-4.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.64 m³·mol⁻¹ChemAxon
Polarizability20.88 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-c3bf4495e8c4abf714dbJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-e3a84538f1dadc72bc00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-000i-9000000000-5d5d6858632925cf1c81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-001i-9000000000-b7dbd311ea9af892ad91JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-3930000000-1af0468e51346890699fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Gu, Heng-da; Shi, Shuang; Yang, Ying; Shi, Zhao-xin; Yu, Zhan-long. Synthesis of acetyl-L-carnitine by direct acylation method. Shenyang Huagong Xueyuan Xuebao (2006), 20(2), 154-155, 160.
External Links:
ResourceLink
CHEBI ID57589
HMDB IDHMDB00201
Pubchem Compound ID18230
Kegg IDC02571
ChemSpider ID21243783
FOODB IDFDB093666
WikipediaAcetylcarnitine
BioCyc ID(-)o-acetylcarnitine

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Carnitine acetylase is specific for short chain fatty acids. Carnitine acetylase seems to affect the flux through the pyruvate dehydrogenase complex. It may be involved as well in the transport of acetyl-CoA into mitochondria
Gene Name:
CAT2
Uniprot ID:
P32796
Molecular weight:
77241.20313
Reactions
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.
General function:
Involved in acyltransferase activity
Specific function:
Involved in the transfer of acetyl-CoA into mitochondria. May also be involved in the metabolism of acetate and of ethanol
Gene Name:
YAT1
Uniprot ID:
P80235
Molecular weight:
77764.79688
Reactions
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.
General function:
Involved in acyltransferase activity
Specific function:
Involved in the shutteling of acetyl-CoA in the cell
Gene Name:
YAT2
Uniprot ID:
P40017
Molecular weight:
103333.0
Reactions
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.