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Record Information
Version1.0
Creation Date2016-09-30 22:26:38 UTC
Update Date2020-06-04 20:33:16 UTC
MCDB ID BMDB0000201
Secondary Accession Numbers
  • BMDB00201
Metabolite Identification
Common NameL-Acetylcarnitine
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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. L-Acetylcarnitine exists in all living species, ranging from bacteria to humans. L-Acetylcarnitine participates in a number of enzymatic reactions, within cattle. In particular, L-Acetylcarnitine and coenzyme A can be biosynthesized from acetyl-CoA and L-carnitine through the action of the enzyme carnitine O-acetyltransferase. In addition, L-Acetylcarnitine and L-carnitine can be converted into acetyl-CoA and coenzyme A; which is catalyzed by the enzyme carnitine O-acetyltransferase. In cattle, L-acetylcarnitine is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. L-Acetylcarnitine has been found to be associated with several diseases known as colorectal cancer, crohn's disease, and 3-hydroxyacyl-coa dehydrogenase deficiency; also l-acetylcarnitine has been linked to several inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency and 3-methyl-crotonyl-glycinuria.
Structure
Thumb
Synonyms
ValueSource
(-)-AcetylcarnitineChEBI
(R)-AcetylcarnitineChEBI
Acetyl-L-(-)-carnitineChEBI
Acetyl-L-carnitineChEBI
L-AcetylcarnitineChEBI
L-Carnitine acetyl esterChEBI
L-O-AcetylcarnitineChEBI
O-Acetyl-(R)-carnitineChEBI
R-AcetylcarnitineChEBI
BranigenMeSH, HMDB
Levocarnitine acetylMeSH, HMDB
Acetyl carnitineMeSH, HMDB
Carnitine, acetylMeSH, HMDB
AlcarMeSH, HMDB
Acetyl L carnitineMeSH, HMDB
Acetylcarnitine, (R)-isomerMeSH, HMDB
MedosanMeSH, HMDB
ALCHMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoateChEBI, HMDB
Acetyl-DL-carnitineChEBI, HMDB
AcetylcarnitineChEBI, HMDB
DL-O-AcetylcarnitineChEBI, HMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoic acidGenerator, HMDB
(+-)-AcetylcarnitineHMDB
Acetyl-carnitineHMDB
ALCARHMDB
NicetileHMDB
O-Acetyl-L-carnitineHMDB
O-AcetylcarnitineHMDB
(3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoateHMDB
C2 CarnitineHMDB
Chemical FormulaC9H17NO4
Average Molecular Weight203.238
Monoisotopic Molecular Weight203.115758031
IUPAC Name(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Nameacetyl-L-carnitine
CAS Registry Number3040-38-8
SMILES
[H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O
InChI Identifier
InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1
InChI KeyRDHQFKQIGNGIED-MRVPVSSYSA-N
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
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability20.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified48 +/- 3 uM details
Detected and Quantified48 +/- 2 uM details
Detected and Quantified48 +/- 5 uM details
Detected and Quantified50 +/- 5 uM details
Detected and Quantified37 +/- 1 uM details
Detected and Quantified39 +/- 2 uM details
Detected and Quantified37 +/- 1 uM details
Detected and Quantified41 +/- 1 uM details
Detected and Quantified51 +/- 13 uM details
Detected and Quantified50 +/- 13 uM details
Detected and Quantified46 +/- 7.4 uM details
HMDB IDHMDB0000201
DrugBank IDDB08842
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093666
KNApSAcK IDNot Available
Chemspider ID5406074
KEGG Compound IDC02571
BioCyc IDO-ACETYLCARNITINE
BiGG IDNot Available
Wikipedia LinkAcetyl-L-carnitine
METLIN IDNot Available
PubChem Compound7045767
PDB IDNot Available
ChEBI ID57589
References
Synthesis ReferenceGu, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  2. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  4. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.