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Record Information
Version1.0
Creation Date2016-09-30 22:19:09 UTC
Update Date2020-06-04 21:20:41 UTC
BMDB IDBMDB0000062
Secondary Accession Numbers
  • BMDB00062
Metabolite Identification
Common NameL-Carnitine
DescriptionL-Carnitine, also known as carnitine d-form, belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine. L-Carnitine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). L-Carnitine participates in a number of enzymatic reactions, within cattle. In particular, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through its interaction with the enzyme carnitine O-acetyltransferase. In addition, Acetyl-CoA and L-carnitine can be converted into L-acetylcarnitine through its interaction with the enzyme carnitine O-acetyltransferase. In cattle, L-carnitine is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway.
Structure
Thumb
Synonyms
ValueSource
(-)-CarnitineChEBI
(-)-L-CarnitineChEBI
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner saltChEBI
CarnicorChEBI
CarniteneChEBI
CarnitineChEBI
CarnitorChEBI
KarnitinChEBI
LevocarnitineChEBI
Vitamin BTChEBI
L-gamma-Trimethyl-beta-hydroxybutyrobetaineKegg
(R)-CarnitineKegg
L-g-Trimethyl-b-hydroxybutyrobetaineGenerator
L-Γ-trimethyl-β-hydroxybutyrobetaineGenerator
(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrateHMDB
(R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxideHMDB
(S)-CarnitineHMDB
1-CarnitineHMDB
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminiumHMDB
3-Hydroxy-4-trimethylammoniobutanoateHMDB
3-Hydroxy-4-trimethylammoniobutanoic acidHMDB
BicarnesineHMDB
CarnikingHMDB
Carniking 50HMDB
CarnileanHMDB
CarnipassHMDB
Carnipass 20HMDB
D-CarnitineHMDB
delta-CarnitineHMDB
DL-CarnitineHMDB
gamma-Trimethyl-ammonium-beta-hydroxybutirateHMDB
gamma-Trimethyl-beta-hydroxybutyrobetaineHMDB
gamma-Trimethyl-hydroxybutyrobetaineHMDB
L-(-)-CarnitineHMDB
LevocarnitinaHMDB
LevocarnitinumHMDB
R-(-)-3-Hydroxy-4-trimethylaminobutyrateHMDB
L CarnitineHMDB
L-CarnitineChEBI
Chemical FormulaC7H15NO3
Average Molecular Weight161.1989
Monoisotopic Molecular Weight161.105193351
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number541-14-0
SMILESNot Available
InChI Identifier
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1
InChI KeyPHIQHXFUZVPYII-ZCFIWIBFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentCarnitines
Alternative Parents
Substituents
  • Carnitine
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Fatty acid
  • Hydroxy acid
  • Tetraalkylammonium salt
  • 1,2-aminoalcohol
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Adipose Tissue
  • Bladder
  • Blood
  • Brain
  • Colostrum
  • Erythrocyte
  • Fibroblasts
  • Heart
  • Intestine
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Lung
  • Mammary Gland
  • Milk
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified1.29 +/- 0.2 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified7 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected and Quantified2.54 +/- 0.51 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified3.14 +/- 0.66 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified6.12 +/- 21.7 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
HeartExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified22 +/- 6 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified1856 +/- 424 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LungExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified346 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified61 +/- 6 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified68 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified68 +/- 5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified62 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified81.36 +/- 20.84 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified72.7 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified77 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified79 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified67 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified85.71 +/- 17.08 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified75.91 +/- 18.17 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified317-437 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1022.66 +/- 63.87 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1072.83 +/- 69.97 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified791-1143 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified829.28 +/- 38.28 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified2600 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified983.18 +/- 45.99 uMNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified3 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Semimembranosus MuscleDetected and Quantified1751 +/- 337 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified20 +/- 6 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00 +/- 0 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected and Quantified6.34 +/- 1.87 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition
details
BloodDetected and Quantified6.67 +/- 2.45 uMNot SpecifiedNot Specified
Transition disease/1 wk after parturition
details
HMDB IDHMDB0000062
DrugBank IDDB00583
Phenol Explorer Compound IDNot Available
FooDB IDFDB000571
KNApSAcK IDNot Available
Chemspider ID2006614
KEGG Compound IDC00318
BioCyc IDCARNITINE
BiGG ID34600
Wikipedia LinkCarnitine
METLIN ID52
PubChem Compound10917
PDB IDNot Available
ChEBI ID16347
References
Synthesis Reference Bols, Mikael; Lundt, Inge; Pedersen, Christian. Simple synthesis of (R)-carnitine from D-galactono-1,4-lactone. Tetrahedron (1992), 48(2), 319-24.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  3. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  4. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  5. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Involved in carnitine O-octanoyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate.
Gene Name:
CROT
Uniprot ID:
O19094
Molecular weight:
70263.0
Reactions
Acetyl-CoA + L-Carnitine → L-Acetylcarnitine + Coenzyme Adetails
L-Acetylcarnitine + L-Carnitine → Acetyl-CoA + Coenzyme Adetails
General function:
Involved in carnitine O-palmitoyltransferase activity
Specific function:
Not Available
Gene Name:
CPT1B
Uniprot ID:
Q58DK1
Molecular weight:
88512.0
Reactions
Palmityl-CoA + L-Carnitine → L-Palmitoylcarnitine + Coenzyme Adetails
Stearoyl-CoA + L-Carnitine → Stearoylcarnitine + Coenzyme Adetails
General function:
Involved in carnitine O-palmitoyltransferase activity
Specific function:
Not Available
Gene Name:
CPT2
Uniprot ID:
Q2KJB7
Molecular weight:
74483.0
Reactions
4,8-Dimethylnonanoyl-CoA + L-Carnitine → 4,8 dimethylnonanoyl carnitine + Coenzyme Adetails
Dodecanoic acid + Coenzyme A → Lauroyl-CoA + L-Carnitinedetails
Palmityl-CoA + L-Carnitine → L-Palmitoylcarnitine + Coenzyme Adetails
Stearoyl-CoA + L-Carnitine → Stearoylcarnitine + Coenzyme Adetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
Gene Name:
TMLHE
Uniprot ID:
Q0VC74
Molecular weight:
49837.0
Reactions
3-Dehydroxycarnitine + Oxoglutaric acid + Oxygen → L-Carnitine + Succinic acid + Carbon dioxidedetails
General function:
Carbohydrate transport and metabolism
Specific function:
High affinity carnitine transporter; the uptake is partially sodium-ion dependent. Thought to mediate the L-carnitine secretion mechanism from testis epididymal epithelium into the lumen which is involved in the maturation of spermatozoa. Also transports organic cations such as tetraethylammonium (TEA) and doxorubicin. The uptake of TEA is inhibited by various organic cations. The uptake of doxorubicin is sodium-independent (By similarity).
Gene Name:
SLC22A16
Uniprot ID:
Q17QN9
Molecular weight:
64355.0