Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2023-05-30 20:55:52 UTC |
---|
HMDB ID | HMDB0000201 |
---|
Secondary Accession Numbers | - HMDB0000456
- HMDB0000515
- HMDB00201
- HMDB00456
- HMDB00515
|
---|
Metabolite Identification |
---|
Common Name | L-Acetylcarnitine |
---|
Description | L-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 | CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C 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 |
---|
Synonyms | Value | Source |
---|
(-)-Acetylcarnitine | ChEBI | (R)-Acetylcarnitine | ChEBI | Acetyl-L-(-)-carnitine | ChEBI | Acetyl-L-carnitine | ChEBI | L-Carnitine acetyl ester | ChEBI | L-O-Acetylcarnitine | ChEBI | O-Acetyl-(R)-carnitine | ChEBI | R-Acetylcarnitine | ChEBI | L-Acetylcarnitine | ChEBI | Branigen | MeSH, HMDB | Levocarnitine acetyl | MeSH, HMDB | Acetyl carnitine | MeSH, HMDB | Carnitine, acetyl | MeSH, HMDB | Alcar | MeSH, HMDB | Acetyl L carnitine | MeSH, HMDB | Acetylcarnitine, (R)-isomer | MeSH, HMDB | Medosan | MeSH, HMDB | ALC | HMDB | 3-(Acetyloxy)-4-(trimethylammonio)butanoate | ChEBI, HMDB | Acetyl-DL-carnitine | ChEBI, HMDB | Acetylcarnitine | ChEBI, HMDB | DL-O-Acetylcarnitine | ChEBI, HMDB | 3-(Acetyloxy)-4-(trimethylammonio)butanoic acid | Generator, HMDB | (+-)-Acetylcarnitine | HMDB | Acetyl-carnitine | HMDB | ALCAR | HMDB | Nicetile | HMDB | O-Acetyl-L-carnitine | HMDB | O-Acetylcarnitine | HMDB | (3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoate | HMDB | C2 Carnitine | HMDB |
|
---|
Chemical Formula | C9H17NO4 |
---|
Average Molecular Weight | 203.238 |
---|
Monoisotopic Molecular Weight | 203.115758031 |
---|
IUPAC Name | (3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate |
---|
Traditional Name | acetyl-L-carnitine |
---|
CAS Registry Number | 3040-38-8 |
---|
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 Key | RDHQFKQIGNGIED-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acid esters |
---|
Direct Parent | Acyl 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 Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | |
---|
Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
---|
[M+H]+ | Astarita_pos | 141.7 | 30932474 | [M+H]+ | MetCCS_test_pos | 142.966 | 30932474 |
|
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9100000000-c3bf4495e8c4abf714db | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Acetylcarnitine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 10V, N/A-QTOF (Annotated) | splash10-000i-9200000000-e3a84538f1dadc72bc00 | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 25V, N/A-QTOF (Annotated) | splash10-000i-9000000000-5d5d6858632925cf1c81 | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - L-Acetylcarnitine Quattro_QQQ 40V, N/A-QTOF (Annotated) | splash10-001i-9000000000-b7dbd311ea9af892ad91 | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - L-Acetylcarnitine , positive-QTOF | splash10-0pb9-3930000000-1af0468e51346890699f | 2018-05-25 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Acetylcarnitine 10V, Positive-QTOF | splash10-0udi-0090000000-71230651236adb31fa6f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Acetylcarnitine 20V, Positive-QTOF | splash10-0f79-9050000000-2a63f200e23202870ebe | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Acetylcarnitine 40V, Positive-QTOF | splash10-000i-9000000000-e9262cbaff8cb4ad0ba6 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2018-05-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View 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 |
---|
| |
Blood | Detected and Quantified | 5.48 +/- 2.15 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 16.540 +/- 3.340 uM | Infant (0-1 year old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 3.00-12.5 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 3.57 (2.91-4.48) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 4.09 +/- 5.83 uM | Children (1-13 years old) | Both | Normal | | details | Blood | Detected and Quantified | 1.30 +/- 0.81 uM | Children (1-13 years old) | Both | Normal | | details | Blood | Detected and Quantified | 6.26 (5.14-7.83) uM | Infant (0-1 year old) | Not Available | Normal | | details | Blood | Detected and Quantified | 8.05(3.22) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 3.00-12.5 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 6.2 +/- 0.6 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 5.7 +/- 0.7 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 6.56 +/- 2.26 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 4.90 (2.48-8.62) uM | Children (1-13 years old) | Both | Normal | | details | Breast Milk | Detected and Quantified | 10.5 +/- 4.7 uM | Adult (>18 years old) | Female | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.322 +/- 0.148 uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.69 +/- 0.33 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.39 +/- 0.2 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.973 +/- 0.002 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.843 +/- 0.441 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 0.955 +/- 0.442 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 1.53 +/- 1.23 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 1.68 +/- 0.780 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.38-1.86 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 0.85 +/- 0.38 umol/mmol creatinine | Newborn (0-30 days old) | Female | Normal | | details | Urine | Detected and Quantified | 0.92 +/- 0.39 umol/mmol creatinine | Newborn (0-30 days old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 4.468 +/- 3.521 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 2.0 (0.4-5.9) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 2.8 (0.6-7.5) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.67 (0.40-1.58) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 7.2058 +/- 6.0635 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 1.928 +/- 0.2829 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected and Quantified | 26.700 +/- 9.700 uM | Infant (0-1 year old) | Not Specified | short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency | | details | Blood | Detected and Quantified | 27.740 +/- 9.800 uM | Infant (0-1 year old) | Female | 3-Hydroxyacyl-CoA dehydrogenase deficiency (SCHAD) | | details | Blood | Detected and Quantified | 26.400 +/- 9.700 uM | Infant (0-1 year old) | Not Specified | Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Blood | Detected and Quantified | 11.9(10-40) uM | Adult (>18 years old) | Both | Sepsis | | details | Blood | Detected and Quantified | 2.83 +/- 4.08 uM | Children (1-13 years old) | Both | Acetaminophen overdose | | details | Blood | Detected and Quantified | 2.5022 (2.2864) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 10.28(3.49) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Blood | Detected and Quantified | 800 +/- 200 uM | Adult (>18 years old) | Both | 3-Methylcrotonyl-CoA Carboxylase Deficiency | | details | Blood | Detected and Quantified | 0.316 (0.091-0.760) uM | Adult (>18 years old) | Both | Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD) | | details | Blood | Detected and Quantified | 6.82 +/- 3.64 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 6.79 +/- 2.28 uM | Children (1-13 years old) | Both | Obesity | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Unclassified IBD | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Tooth Decay | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal adenoma | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal adenoma | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | Urine | Detected and Quantified | 9.443 +/- 12.772 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 6.5552 +/- 13.7484 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 6.3512 +/- 10.4433 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Very Long Chain Acyl-CoA Dehydrogenase Deficiency |
---|
- 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 |
---|
- 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 ]
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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 |
---|
- 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)
|
---|
External Links |
---|
DrugBank ID | DB08842 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB093666 |
---|
KNApSAcK ID | C00052178 |
---|
Chemspider ID | 5406074 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | O-ACETYLCARNITINE |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Acetyl-L-carnitine |
---|
METLIN ID | Not Available |
---|
PubChem Compound | Not Available |
---|
PDB ID | Not Available |
---|
ChEBI ID | 57589 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | MDB00000096 |
---|
Good Scents ID | rw1654391 |
---|
References |
---|
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. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - 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 ]
- Sakuma T: Alteration of urinary carnitine profile induced by benzoate administration. Arch Dis Child. 1991 Jul;66(7):873-5. [PubMed:1863104 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Deufel T: Determination of L-carnitine in biological fluids and tissues. J Clin Chem Clin Biochem. 1990 May;28(5):307-11. [PubMed:2380667 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
---|