Showing metabocard for L-Acetylcarnitine (BMDB0000201)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:26:38 UTC
Update Date2020-06-04 20:33:16 UTC
BMDB IDBMDB0000201
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-AcetylcarnitineChEBI
(R)-AcetylcarnitineChEBI
Acetyl-L-(-)-carnitineChEBI
Acetyl-L-carnitineChEBI
L-Carnitine acetyl esterChEBI
L-O-AcetylcarnitineChEBI
O-Acetyl-(R)-carnitineChEBI
R-AcetylcarnitineChEBI
L-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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
  • Peroxisome
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-c3bf4495e8c4abf714dbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-e3a84538f1dadc72bc00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-000i-9000000000-5d5d6858632925cf1c81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-001i-9000000000-b7dbd311ea9af892ad91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-3930000000-1af0468e51346890699fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-71230651236adb31fa6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-9050000000-2a63f200e23202870ebeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Brain
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Neuron
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected and Quantified0.96 +/- 0.36 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified0.65-1.09 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected and Quantified5 +/- 2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Longissimus Thoracis MuscleDetected and Quantified854 +/- 153 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified1892 +/- 398 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified45.97 +/- 7.39 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified48 +/- 3 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified48 +/- 2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified48 +/- 5 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified50 +/- 5 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected and Quantified51.71 +/- 12.86 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified37 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified39 +/- 2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified37 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified41 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified49.66 +/- 12.65 uMNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.24 +/- 0.11 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified871 +/- 150 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified1612 +/- 318 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified40 +/- 11 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0304631
DrugBank IDDB08842
Phenol Explorer Compound IDNot Available
FooDB IDFDB093666
KNApSAcK IDC00052178
Chemspider ID5406074
KEGG Compound IDNot Available
BioCyc IDO-ACETYLCARNITINE
BiGG IDNot Available
Wikipedia LinkAcetyl-L-carnitine
METLIN IDNot Available
PubChem CompoundNot Available
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.

Enzymes

Enzyme Details
1. Peroxisomal carnitine O-octanoyltransferase
General function:
Involved in carnitine O-octanoyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate.
Gene Name:
CROT
Uniprot ID:
O19094
Molecular weight:
70263.0
Reactions
Acetyl-CoA + L-Carnitine → L-Acetylcarnitine + Coenzyme Adetails
L-Acetylcarnitine + L-Carnitine → Acetyl-CoA + Coenzyme Adetails