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Record Information
Version1.0
Creation Date2016-07-13 19:42:10 UTC
Update Date2021-04-30 20:57:58 UTC
LmdbLMDB00091
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Acetylcarnitine
DescriptionL-Acetylcarnitine is an acetic acid ester of carnitine that facilitates movement of acetyl CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. In addition to his metabolic role, acetyl-L-carnitine (ALC) posses unique neuroprotective, neuromodulatory, and neurotrophic properties this may play an important role in counteracting various disease processes. (PubMed ID 15363640).
Structure
Thumb
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 Weight203.2356
Monoisotopic Molecular Weight203.115758037
IUPAC Name(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Nameacetyl-L-carnitine
CAS Registry Number3040-38-8
SMILES
CC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3
InChI KeyRDHQFKQIGNGIED-UHFFFAOYSA-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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-c3bf4495e8c4abf714dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-e3a84538f1dadc72bc00Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-000i-9000000000-5d5d6858632925cf1c81Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-001i-9000000000-b7dbd311ea9af892ad91Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pb9-3930000000-1af0468e51346890699fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-71230651236adb31fa6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-9050000000-2a63f200e23202870ebeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
  • Plasma
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
PlasmaDetected and Quantified0.96 +/- 0.36 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Sergio Polakof, D...
details
SerumDetected and Quantified10.51 +/- 2.1153 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.101 +/- 1.8262 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified11.3543 +/- 4.2601 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.3715 +/- 2.397 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.5225 +/- 1.3105 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.19 +/- 3.63 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified8.9183 +/- 4.7964 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.0763 +/- 2.2167 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.2359 +/- 1.5761 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.9667 +/- 2.8578 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.1042 +/- 2.6787 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified3.44 +/- 1.38 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified6.9588 +/- 2.7243 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.6116 +/- 1.9567 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.3333 +/- 2.8185 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.3472 +/- 1.4752 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.9043 +/- 2.5292 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.5448 +/- 3.9193 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.4563 +/- 1.6895 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.477 +/- 2.3139 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.8555 +/- 2.3597 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified8.8195 +/- 0.4984 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.1829 +/- 3.1178 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.2543 +/- 5.9303 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified12.3329 +/- 5.8573 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.3592 +/- 3.5924 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.9315 +/- 2.2176 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified12.5995 +/- 7.0744 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified8.1167 +/- 3.8442 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.6671 +/- 3.8185 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.5491 +/- 2.652 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected and Quantified8.2878 +/- 5.4392 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.1825 +/- 2.6147 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified10.8323 +/- 3.4144 uM
Normal
Ovine
    • Goldansaz et al.,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
DrugBank IDDB08842
HMDB IDHMDB0304631
FooDB IDFDB093666
Phenol Explorer IDNot Available
KNApSAcK IDC00052178
BiGG IDNot Available
BioCyc IDO-ACETYLCARNITINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcetyl-L-carnitine
Chemspider ID5406074
ChEBI ID57589
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDYMDB00351
ECMDB IDECMDB24022
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available