Human Metabolome Database: Showing metabocard for L-Acetylcarnitine (HMDB0000201)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-04-23 20:54:49 UTC

HMDB ID

HMDB0000201

Secondary Accession Numbers

HMDB0000456
HMDB0000515
HMDB00201
HMDB00456
HMDB00515

Metabolite Identification

Common Name

L-Acetylcarnitine

Description

L-Acetylcarnitine (ALCAR or ALC) 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. In addition to his metabolic role, L-acetylcarnitine posses unique neuroprotective, neuromodulatory, and neurotrophic properties. This may play an important role in counteracting various disease processes (PMID: 15363640 ). L-Acetylcarnitine has been identified in the human placenta (PMID: 32033212 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Acetylcarnitine	ChEBI
(R)-Acetylcarnitine	ChEBI
Acetyl-L-(-)-carnitine	ChEBI
Acetyl-L-carnitine	ChEBI
L-Acetylcarnitine	ChEBI
L-Carnitine acetyl ester	ChEBI
L-O-Acetylcarnitine	ChEBI
O-Acetyl-(R)-carnitine	ChEBI
R-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

O-acetylcarnitine (CHEBI:57589 )
O-acyl-L-carnitine (CHEBI:57589 )

Ontology

Very long chain acyl-coa dehydrogenase deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical process:

Cellular process:

Cell signaling

Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	145 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	20.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-c3bf4495e8c4abf714db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-9200000000-e3a84538f1dadc72bc00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000i-9000000000-5d5d6858632925cf1c81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-001i-9000000000-b7dbd311ea9af892ad91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0pb9-3930000000-1af0468e51346890699f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	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

Name	SMPDB/Pathwhiz	KEGG
Beta Oxidation of Very Long Chain Fatty Acids
Oxidation of Branched Chain Fatty Acids		Not Available
Adrenoleukodystrophy, X-linked		Not Available
Carnitine-acylcarnitine translocase deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.48 +/- 2.15 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	16.540 +/- 3.340 uM	Infant (0-1 year old)	Not Specified	Normal	11489939	details
Blood	Detected and Quantified	3.00-12.5 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	3.57 (2.91-4.48) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	4.09 +/- 5.83 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	1.30 +/- 0.81 uM	Children (1-13 years old)	Both	Normal	24521011	details
Blood	Detected and Quantified	6.26 (5.14-7.83) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	8.05(3.22) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	3.00-12.5 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	6.2 +/- 0.6 uM	Adult (>18 years old)	Male	Normal	12905800	details
Blood	Detected and Quantified	5.7 +/- 0.7 uM	Adult (>18 years old)	Female	Normal	12905800	details
Blood	Detected and Quantified	6.56 +/- 2.26 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	4.90 (2.48-8.62) uM	Children (1-13 years old)	Both	Normal	9034211	details
Breast Milk	Detected and Quantified	10.5 +/- 4.7 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.322 +/- 0.148 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	26476344	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	0.69 +/- 0.33 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.39 +/- 0.2 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected but not Quantified		Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.973 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.843 +/- 0.441 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.955 +/- 0.442 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.53 +/- 1.23 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.68 +/- 0.780 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	22727327	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	17022649	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21177801	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	0.38-1.86 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	López Hernández Y...	details
Urine	Detected and Quantified	0.85 +/- 0.38 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	López Hernández Y...	details
Urine	Detected and Quantified	0.92 +/- 0.39 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	López Hernández Y...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	4.468 +/- 3.521 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	2.0 (0.4-5.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.8 (0.6-7.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	7.2058 +/- 6.0635 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	1.928 +/- 0.2829 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	12905800	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	26.700 +/- 9.700 uM	Infant (0-1 year old)	Not Specified	short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency	11489939	details
Blood	Detected and Quantified	27.740 +/- 9.800 uM	Infant (0-1 year old)	Female	3-Hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)	11489939	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	11489939	details
Blood	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected and Quantified	2.83 +/- 4.08 uM	Children (1-13 years old)	Both	Acetaminophen overdose	24521011	details
Blood	Detected and Quantified	2.5022 (2.2864) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	10.28(3.49) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	800 +/- 200 uM	Adult (>18 years old)	Both	3-Methylcrotonyl-CoA Carboxylase Deficiency	25732994	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)	9034211	details
Blood	Detected and Quantified	6.82 +/- 3.64 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	6.79 +/- 2.28 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Feces	Detected but not Quantified		Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified		Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified		Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Tooth Decay	31026179	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Bladder cancer	21799048	details
Urine	Detected and Quantified	9.443 +/- 12.772 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	6.5552 +/- 13.7484 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected and Quantified	6.3512 +/- 10.4433 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	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 ]
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
(). Mordechai, Hien, and David S. Wishart. .

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

Not Available

Chemspider ID

5406074

KEGG Compound ID

C02571

BioCyc ID

O-ACETYLCARNITINE

BiGG ID

Not Available

Wikipedia Link

Acetyl-L-carnitine

METLIN ID

Not Available

PubChem Compound

7045767

PDB ID

Not Available

ChEBI ID

57589

Food Biomarker Ontology

Not Available

VMH ID

ACRN

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

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 ]
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Enzymes

Enzyme Details

1. Carnitine O-acetyltransferase

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-Acetylcarnitine	details

Enzyme Details

2. Mitochondrial carnitine/acylcarnitine carrier protein

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

Showing metabocard for L-Acetylcarnitine (HMDB0000201)

Structure for HMDB0000201 (L-Acetylcarnitine)

Enzymes

Reactions