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Record Information
Version1.0
Creation Date2016-07-13 19:40:46 UTC
Update Date2021-04-30 20:57:58 UTC
LmdbLMDB00027
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Carnitine
DescriptionCarnitine is not an essential amino acid; it can be synthesized in the body. However, it is so important in providing energy to muscles including the heart-that some researchers are now recommending carnitine supplements in the diet, particularly for people who do not consume much red meat, the main food source for carnitine. Carnitine has been described as a vitamin, an amino acid, or a metabimin, i.e., an essential metabolite. Like the B vitamins, carnitine contains nitrogen and is very soluble in water, and to some researchers carnitine is a vitamin (Liebovitz 1984). It was found that an animal (yellow mealworm) could not grow without carnitine in its diet. However, as it turned out, almost all other animals, including animals, do make their own carnitine; thus, it is no longer considered a vitamin. Nevertheless, in certain circumstances-such as deficiencies of methionine, lysine or vitamin C or kidney dialysis--carnitine shortages develop. Under these conditions, carnitine must be absorbed from food, and for this reason it is sometimes referred to as a "metabimin" or a conditionally essential metabolite. Like the other amino acids used or manufactured by the body, carnitine is an amine. But like choline, which is sometimes considered to be a B vitamin, carnitine is also an alcohol (specifically, a trimethylated carboxy-alcohol). Thus, carnitine is an unusual amino acid and has different functions than most other amino acids, which are most usually employed by the body in the construction of protein. Carnitine is an essential factor in fatty acid metabolism in mammals. It's most important known metabolic function is to transport fat into the mitochondria of muscle cells, including those in the heart, for oxidation. This is how the heart gets most of its energy. In animals, about 25% of carnitine is synthesized in the liver, kidney and brain from the amino acids lysine and methionine. Most of the carnitine in the body comes from dietary sources such as red meat and dairy products. Inborn errors of carnitine metabolism can lead to brain deterioration like that of Reye's syndrome, gradually worsening muscle weakness, Duchenne-like muscular dystrophy and extreme muscle weakness with fat accumulation in muscles. Borurn et al. (1979) describe carnitine as an essential nutrient for pre-term babies, certain types (non-ketotic) of hypoglycemics, kidney dialysis patients, cirrhosis, and in kwashiorkor, type IV hyperlipidemia, heart muscle disease (cardiomyopathy), and propionic or organic aciduria (acid urine resulting from genetic or other anomalies). In all these conditions and the inborn errors of carnitine metabolism, carnitine is essential to life and carnitine supplements are valuable. carnitine therapy may also be useful in a wide variety of clinical conditions. carnitine supplementation has improved some patients who have angina secondary to coronary artery disease. It may be worth a trial in any form of hyperlipidemia or muscle weakness. carnitine supplements may be useful in many forms of toxic or metabolic liver disease and in cases of heart muscle disease. Hearts undergoing severe arrhythmia quickly deplete their stores of carnitine. Athletes, particularly in Europe, have used carnitine supplements for improved endurance. carnitine may improve muscle building by improving fat utilization and may even be useful in treating obesity. carnitine joins a long list of nutrients which may be of value in treating pregnant women, hypothyroid individuals, and male infertility due to low motility of sperm. Even the Physician's Desk Reference gives indication for carnitine supplements as "improving the tolerance of ischemic heart disease, myocardial insufficiencies, and type IV hyperlipoproteinemia. carnitine deficiency is noted in abnormal liver function, renal dialysis patients, and severe to moderate muscular weakness with associated anorexia." (http://www.dcnutrition.com).
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 Name(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Traditional NameL-carnitine
CAS Registry Number541-15-1
SMILES
C[N+](C)(C)C[C@H](O)CC([O-])=O
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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ALOGPS
logP-4.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.49 m³·mol⁻¹ChemAxon
Polarizability16.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-1b25dacb04c3ed5be8d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9100000000-c15eaa190d1e28a4839aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-9b579c570aab7c7d3a21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ik9-0900000000-e37d3def2de1af5bd2f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ue9-8900000000-cf37f0a721cd52d86e8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0r0c-9200000000-a11a4872036f3c33d25aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4l-9000000000-2402e260a330ff1772a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0w29-6900000000-d0136248acdd706e650bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-2900000000-61732bb10307f2b183caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zg0-9400000000-15c3db3324f1d46d3c7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-2900000000-ee79f10dce9fc09246ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-3bffd5143cf8b072299eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-0900000000-e68f553bcb15d3ef5b47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-c5b43723951af6da48cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-dd1b1a023937cdcb11afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-3900000000-9f24d3bc535736149e2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-632ef17d9dde38586990Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-97af6636a917c0edea61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pc-9300000000-543e21cb6b9785149e31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9000000000-9128d6fe96d9c7276695Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Lung
  • Meat
  • Milk
  • Plasma
  • Serum
  • Synovial Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
LungDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected and Quantified1022.66 +/- 63.87 uMNot AvailableBovine details
MeatDetected and Quantified1072.83 +/- 69.97 uMNot AvailableBovine details
MeatDetected and Quantified829.28 +/- 38.28 uMNot AvailableBovine details
MeatDetected and Quantified983.18 +/- 45.99 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified346 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected and Quantified6.12 +/- 21.7 uMNot AvailableBovine details
PlasmaDetected and Quantified0.00 +/- 0 uMNot AvailableBovine details
PlasmaDetected and Quantified1.29 +/- 0.2 uMNot AvailableBovine details
PlasmaDetected and Quantified2.54 +/- 0.51 uMNot AvailableBovine details
PlasmaDetected and Quantified3.14 +/- 0.66 uMNot AvailableBovine details
PlasmaDetected and Quantified6.34 +/- 1.87 uMNot AvailableBovine details
PlasmaDetected and Quantified6.67 +/- 2.45 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified48.251 +/- 12.9226 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified36.9763 +/- 7.0966 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified31.5666 +/- 11.4135 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified44.7269 +/- 15.9769 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified40.0263 +/- 10.8219 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified39.0586 +/- 15.3407 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.3899 +/- 12.2303 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified19.36 +/- 7.31 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified19.29 +/- 9.01 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified30.5504 +/- 7.1397 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified43.6222 +/- 13.5638 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified32.3627 +/- 12.6131 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified45.0218 +/- 19.1083 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified35.3238 +/- 10.6378 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified26.7408 +/- 9.636 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified35.2382 +/- 14.6668 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified46.282 +/- 15.1681 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified36.5635 +/- 15.8798 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified37.2006 +/- 11.658 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified28.6083 +/- 10.2109 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified30.3285 +/- 12.5693 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified28.4499 +/- 4.6495 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected and Quantified41.6641 +/- 13.9143 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified43.7626 +/- 15.1365 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.0963 +/- 7.1923 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.2262 +/- 10.5963 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified42.2529 +/- 14.9342 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified30.2502 +/- 6.7861 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.5043 +/- 11.9146 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified52.4049 +/- 15.37 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified35.0364 +/- 11.6127 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified42.9042 +/- 14.4074 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified31.3116 +/- 7.0153 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified41.2464 +/- 11.4395 uM
Normal
Ovine
    • Goldansaz et al.,...
details
Synovial FluidDetected but not QuantifiedNot ApplicableNot AvailableOvine details
DrugBank IDDB00583
HMDB IDHMDB0000062
FooDB IDFDB000571
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34600
BioCyc IDCARNITINE
METLIN ID52
PDB IDNot Available
Wikipedia LinkCarnitine
Chemspider ID2006614
ChEBI ID16347
PubChem Compound ID10917
Kegg Compound IDC00318
YMDB IDYMDB00616
ECMDB IDECMDB23900
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available