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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:52 UTC
HMDB IDHMDB0000201
Secondary Accession Numbers
  • HMDB0000456
  • HMDB0000515
  • HMDB00201
  • HMDB00456
  • HMDB00515
Metabolite Identification
Common NameL-Acetylcarnitine
DescriptionL-Acetylcarnitine (Acetylcarnitine or ALC or LAC) is an acetic acid ester of carnitine that facilitates the movement of acetyl-CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. Acetylcarnitine is an endogenous compound widely distributed in many tissues, including brain. Chemically, acetylcarnitine is the acetylated derivative of the amino acid L-carnitine whose function is generally correlated with regulation of energy metabolism within mitochondria. The synthesis of acetylcarnitine is catalyzed by the enzyme carnitine acetyltransferase (CAT), which is located on the inner mitochondrial membrane as well as in endoplasmic reticulum and peroxisome. CAT promotes the transfer of an acetyl group from acetyl-Coenzyme A (acetyl-CoA) to carnitine, thereby producing acetylcarnitine and free CoA (PMID: 29267192 ). After being synthetized, acetylcarnitine is transported outside mitochondria into the cytosol by the enzyme carnitine/acetylcarnitine translocase (CACT). This is a crucial metabolic reaction for beta-oxidation of fatty acids whereby acetylcarnitine facilitates the transport of acetyl-CoA across mitochondrial membranes (PMID: 29267192 ). In addition to his metabolic role, L-acetylcarnitine possesses unique neuroprotective, neuromodulatory, and neurotrophic properties. acetylcarnitine is mobile throughout the plasma membranes and can rapidly cross blood-brain barrier. Indeed, acetylcarnitine can be transported by the high-affinity sodium-dependent organic cation/transporter (OCTN2), which is functionally expressed in cells forming the blood-brain barrier (PMID: 29267192 ). A wide range of mechanisms have been proposed to explain the multiplicity of acetylcarnitine activities within nervous tissues. In particular, it has been demonstrated that acetylcarnitine modulates the activity of nerve growth factor (NGF) and enhances the expression of NGF receptors in striatum/hippocampus during development (PMID: 29267192 ). Moreover, acetylcarnitine modulates different neurotransmitter systems, including the GABAergic, dopaminergic, and cholinergic system by increasing acetyl-CoA content and choline acetyltransferase (ChAT) activity. This may play an important role in counteracting various neurodegenerative disease processes (PMID: 15363640 ).  In rodent models, L-acetylcarnitine has been found to be critical for hippocampal function and to induce rapid and lasting antidepressant-like effects via epigenetic mechanisms of histone acetylation (PMID: 30061399 ). More recently, levels of acetylcarnitine have been found to be reduced in people with major depressive disorder (MDD) (PMID: 30061399 ). In contrast to the positive neurotrophic effects for L-acetylcarnitine, it has been found that high blood levels of acetylcarnitine (>12 µmol/L) can be associated with inflammation or infection. Increases in acylcarnitine levels, especially for short-chain acylcarnitines such as acetylcarnitine appear to arise from the release of these compounds from the liver during infection or periods of stress/trauma. This is done to support increased levels of fatty acid beta-oxidation, which is needed for the production and synthesis of B and T-cells (macrophages, neutrophils) to fight infections or traumatic injuries. Interestingly, those suffering from sepsis or septicemia can have very high L-acetylcarnitine levels. It has been found that those with L-acetylcarnitine levels >20 µmol/L have up to 5X greater risk of dying (PMID: 30379669 ). This likely reflects a severe dysregulation of acylcarnitine production from a dysregulated immune system or damage to the liver. Overall, levels of L-acetylcarnitine correlate with the severity of organ dysfunction, inflammation and infection in sepsis and can serve as a prognostic biomarker for mortality prediction.
Structure
Data?1676999676
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
CC(=O)O[C@H](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/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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-4.031 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Astarita_pos141.730932474
[M+H]+MetCCS_test_pos142.96630932474
Predicted Molecular 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
Polarizability20.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+149.1830932474
DeepCCS[M-H]-147.05830932474
DeepCCS[M-2H]-180.29630932474
DeepCCS[M+Na]+155.09230932474
AllCCS[M+H]+145.932859911
AllCCS[M+H-H2O]+142.532859911
AllCCS[M+NH4]+149.132859911
AllCCS[M+Na]+150.032859911
AllCCS[M-H]-153.832859911
AllCCS[M+Na-2H]-155.132859911
AllCCS[M+HCOO]-156.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-AcetylcarnitineCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C2322.9Standard polar33892256
L-AcetylcarnitineCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C1232.0Standard non polar33892256
L-AcetylcarnitineCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C1468.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Acetylcarnitine,1TMS,isomer #1CC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C1424.0Semi standard non polar33892256
L-Acetylcarnitine,1TBDMS,isomer #1CC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C1660.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-c3bf4495e8c4abf714db2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-000i-9200000000-e3a84538f1dadc72bc002018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-000i-9000000000-5d5d6858632925cf1c812018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-001i-9000000000-b7dbd311ea9af892ad912018-05-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Acetylcarnitine , positive-QTOFsplash10-0pb9-3930000000-1af0468e51346890699f2018-05-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Acetylcarnitine 10V, Positive-QTOFsplash10-0udi-0090000000-71230651236adb31fa6f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Acetylcarnitine 20V, Positive-QTOFsplash10-0f79-9050000000-2a63f200e23202870ebe2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Acetylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2018-05-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
  • Peroxisome
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Neuron
  • Placenta
  • Prostate
  • Semen
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.48 +/- 2.15 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified16.540 +/- 3.340 uMInfant (0-1 year old)Not Specified
Normal
details
BloodDetected and Quantified3.00-12.5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.57 (2.91-4.48) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.09 +/- 5.83 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified1.30 +/- 0.81 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified6.26 (5.14-7.83) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified8.05(3.22) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.00-12.5 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified6.2 +/- 0.6 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified5.7 +/- 0.7 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified6.56 +/- 2.26 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.90 (2.48-8.62) uMChildren (1-13 years old)BothNormal details
Breast MilkDetected and Quantified10.5 +/- 4.7 uMAdult (>18 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.322 +/- 0.148 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.69 +/- 0.33 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.39 +/- 0.2 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.973 +/- 0.002 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified0.843 +/- 0.441 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.955 +/- 0.442 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.53 +/- 1.23 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.68 +/- 0.780 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.38-1.86 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.85 +/- 0.38 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.92 +/- 0.39 umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.468 +/- 3.521 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified2.0 (0.4-5.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.8 (0.6-7.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.67 (0.40-1.58) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
UrineDetected and Quantified7.2058 +/- 6.0635 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified1.928 +/- 0.2829 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified26.700 +/- 9.700 uMInfant (0-1 year old)Not Specified
short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency
details
BloodDetected and Quantified27.740 +/- 9.800 uMInfant (0-1 year old)Female
3-Hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)
details
BloodDetected and Quantified26.400 +/- 9.700 uMInfant (0-1 year old)Not Specified
Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
BloodDetected and Quantified11.9(10-40) uMAdult (>18 years old)BothSepsis details
BloodDetected and Quantified2.83 +/- 4.08 uMChildren (1-13 years old)Both
Acetaminophen overdose
details
BloodDetected and Quantified2.5022 (2.2864) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified10.28(3.49) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified800 +/- 200 uMAdult (>18 years old)Both3-Methylcrotonyl-CoA Carboxylase Deficiency details
BloodDetected and Quantified0.316 (0.091-0.760) uMAdult (>18 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
BloodDetected and Quantified6.82 +/- 3.64 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified6.79 +/- 2.28 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleTooth Decay details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
UrineDetected and Quantified9.443 +/- 12.772 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified6.5552 +/- 13.7484 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
UrineDetected and Quantified6.3512 +/- 10.4433 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
3-Methyl-crotonyl-glycinuria
  1. Thomsen JA, Lund AM, Olesen JH, Mohr M, Rasmussen J: Is L-Carnitine Supplementation Beneficial in 3-Methylcrotonyl-CoA Carboxylase Deficiency? JIMD Rep. 2015;21:79-88. doi: 10.1007/8904_2014_393. Epub 2015 Mar 3. [PubMed:25732994 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency
  1. Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
3-Hydroxyacyl-CoA dehydrogenase deficiency
  1. Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
Sepsis
  1. Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
  • 114500 (Colorectal cancer)
  • 210200 (3-Methyl-crotonyl-glycinuria)
  • 601665 (Obesity)
  • 231530 (3-Hydroxyacyl-CoA dehydrogenase deficiency)
  • 266600 (Crohn's disease)
  • 610247 (Eosinophilic esophagitis)
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000096
Good Scents IDrw1654391
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. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Sakuma T: Alteration of urinary carnitine profile induced by benzoate administration. Arch Dis Child. 1991 Jul;66(7):873-5. [PubMed:1863104 ]
  3. Grizard G, Lombard-Vignon N, Boucher D: Changes in carnitine and acetylcarnitine in human semen during cryopreservation. Hum Reprod. 1992 Oct;7(9):1245-8. [PubMed:1479006 ]
  4. Kamimori H, Hamashima Y, Konishi M: Determination of carnitine and saturated-acyl group carnitines in human urine by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1994 May 1;218(2):417-24. [PubMed:8074302 ]
  5. Cooper MB, Forte CA, Jones DA: Citrate interference with the determination of acetylcarnitine: a method for its elimination. Clin Chim Acta. 1986 Sep 30;159(3):291-9. [PubMed:3769216 ]
  6. Spagnoli A, Lucca U, Menasce G, Bandera L, Cizza G, Forloni G, Tettamanti M, Frattura L, Tiraboschi P, Comelli M, et al.: Long-term acetyl-L-carnitine treatment in Alzheimer's disease. Neurology. 1991 Nov;41(11):1726-32. [PubMed:1944900 ]
  7. Brooks DE: Carnitine, acetylcarnitine and the activity of carnitine acyltransferases in seminal plasma and spermatozoa of men, rams and rats. J Reprod Fertil. 1979 Jul;56(2):667-73. [PubMed:480318 ]
  8. Inoue F, Terada N, Nakajima H, Okochi M, Kodo N, Kizaki Z, Kinugasa A, Sawada T: Effect of sports activity on carnitine metabolism. Measurement of free carnitine, gamma-butyrobetaine and acylcarnitines by tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):83-8. [PubMed:10491992 ]
  9. Niu YJ, Jiang ZM, Shu H, Li CF, Liu W, Yao GX, Jiang J, Li JQ, Longo A: [Assay of carnitine in plasma and urine of healthy adults]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2002 Apr;24(2):185-7. [PubMed:12905800 ]
  10. Siliprandi N, Di Lisa F, Pieralisi G, Ripari P, Maccari F, Menabo R, Giamberardino MA, Vecchiet L: Metabolic changes induced by maximal exercise in human subjects following L-carnitine administration. Biochim Biophys Acta. 1990 Apr 23;1034(1):17-21. [PubMed:2328258 ]
  11. Marzo A, Cardace G, Corbelleta C, Bassani E, Morabito E, Arrigoni Martelli E: Homeostatic equilibrium of L-carnitine family before and after i.v. administration of propionyl-L-carnitine in humans, dogs and rats. Eur J Drug Metab Pharmacokinet. 1991;Spec No 3:357-63. [PubMed:1820908 ]
  12. Novak M, Wieser PB, Buch M, Hahn P: Acetylcarnitine and free carnitine in body fluids before and after birth. Pediatr Res. 1979 Jan;13(1):10-5. [PubMed:571081 ]
  13. Battistin L, Pizzolato G, Dam M, Da Col C, Perlotto N, Saitta B, Borsato N, Calvani M, Ferlin G: Single-photon emission computed tomography studies with 99mTc-hexamethylpropyleneamine oxime in dementia: effects of acute administration of L-acetylcarnitine. Eur Neurol. 1989;29(5):261-5. [PubMed:2792144 ]
  14. Deufel T: Determination of L-carnitine in biological fluids and tissues. J Clin Chem Clin Biochem. 1990 May;28(5):307-11. [PubMed:2380667 ]
  15. Minkler PE, Hoppel CL: Quantification of free carnitine, individual short- and medium-chain acylcarnitines, and total carnitine in plasma by high-performance liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):510-8. [PubMed:8214594 ]
  16. Bruno G, Scaccianoce S, Bonamini M, Patacchioli FR, Cesarino F, Grassini P, Sorrentino E, Angelucci L, Lenzi GL: Acetyl-L-carnitine in Alzheimer disease: a short-term study on CSF neurotransmitters and neuropeptides. Alzheimer Dis Assoc Disord. 1995 Fall;9(3):128-31. [PubMed:8534410 ]
  17. Pace S, Longo A, Toon S, Rolan P, Evans AM: Pharmacokinetics of propionyl-L-carnitine in humans: evidence for saturable tubular reabsorption. Br J Clin Pharmacol. 2000 Nov;50(5):441-8. [PubMed:11069438 ]
  18. De Rosa M, Boggia B, Amalfi B, Zarrilli S, Vita A, Colao A, Lombardi G: Correlation between seminal carnitine and functional spermatozoal characteristics in men with semen dysfunction of various origins. Drugs R D. 2005;6(1):1-9. [PubMed:15801863 ]
  19. Zanelli SA, Solenski NJ, Rosenthal RE, Fiskum G: Mechanisms of ischemic neuroprotection by acetyl-L-carnitine. Ann N Y Acad Sci. 2005 Aug;1053:153-61. [PubMed:16179519 ]
  20. Kuratsune H, Yamaguti K, Lindh G, Evengard B, Hagberg G, Matsumura K, Iwase M, Onoe H, Takahashi M, Machii T, Kanakura Y, Kitani T, Langstrom B, Watanabe Y: Brain regions involved in fatigue sensation: reduced acetylcarnitine uptake into the brain. Neuroimage. 2002 Nov;17(3):1256-65. [PubMed:12414265 ]
  21. Gray SC, Devito G, Nimmo MA: Effect of active warm-up on metabolism prior to and during intense dynamic exercise. Med Sci Sports Exerc. 2002 Dec;34(12):2091-6. [PubMed:12471321 ]
  22. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  23. Virmani A, Binienda Z: Role of carnitine esters in brain neuropathology. Mol Aspects Med. 2004 Oct-Dec;25(5-6):533-49. doi: 10.1016/j.mam.2004.06.003. [PubMed:15363640 ]
  24. Nasca C, Bigio B, Lee FS, Young SP, Kautz MM, Albright A, Beasley J, Millington DS, Mathe AA, Kocsis JH, Murrough JW, McEwen BS, Rasgon N: Acetyl-l-carnitine deficiency in patients with major depressive disorder. Proc Natl Acad Sci U S A. 2018 Aug 21;115(34):8627-8632. doi: 10.1073/pnas.1801609115. Epub 2018 Jul 30. [PubMed:30061399 ]
  25. Chiechio S, Canonico PL, Grilli M: l-Acetylcarnitine: A Mechanistically Distinctive and Potentially Rapid-Acting Antidepressant Drug. Int J Mol Sci. 2017 Dec 21;19(1). pii: ijms19010011. doi: 10.3390/ijms19010011. [PubMed:29267192 ]
  26. Chung KP, Chen GY, Chuang TY, Huang YT, Chang HT, Chen YF, Liu WL, Chen YJ, Hsu CL, Huang MT, Kuo CH, Yu CJ: Increased Plasma Acetylcarnitine in Sepsis Is Associated With Multiple Organ Dysfunction and Mortality: A Multicenter Cohort Study. Crit Care Med. 2019 Feb;47(2):210-218. doi: 10.1097/CCM.0000000000003517. [PubMed:30379669 ]
  27. Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]

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:
CRAT
Uniprot ID:
P43155
Molecular weight:
70875.095
Reactions
Acetyl-CoA + L-Carnitine → Coenzyme A + L-Acetylcarnitinedetails
General function:
Involved in transporter activity
Specific function:
Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:
SLC25A20
Uniprot ID:
O43772
Molecular weight:
32943.46