Livestock Metabolome Database: Showing metabocard for L-Carnitine (LMDB00027)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:46 UTC

Update Date

2021-04-30 20:57:58 UTC

Lmdb

LMDB00027

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-Carnitine

Description

Carnitine 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(-)-Carnitine	ChEBI
(-)-L-Carnitine	ChEBI
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt	ChEBI
Carnicor	ChEBI
Carnitene	ChEBI
Carnitine	ChEBI
Carnitor	ChEBI
Karnitin	ChEBI
Levocarnitine	ChEBI
Vitamin BT	ChEBI
L-gamma-Trimethyl-beta-hydroxybutyrobetaine	Kegg
(R)-Carnitine	Kegg
L-g-Trimethyl-b-hydroxybutyrobetaine	Generator
L-Γ-trimethyl-β-hydroxybutyrobetaine	Generator
(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate	HMDB
(R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide	HMDB
(S)-Carnitine	HMDB
1-Carnitine	HMDB
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium	HMDB
3-Hydroxy-4-trimethylammoniobutanoate	HMDB
3-Hydroxy-4-trimethylammoniobutanoic acid	HMDB
Bicarnesine	HMDB
Carniking	HMDB
Carniking 50	HMDB
Carnilean	HMDB
Carnipass	HMDB
Carnipass 20	HMDB
D-Carnitine	HMDB
delta-Carnitine	HMDB
DL-Carnitine	HMDB
gamma-Trimethyl-ammonium-beta-hydroxybutirate	HMDB
gamma-Trimethyl-beta-hydroxybutyrobetaine	HMDB
gamma-Trimethyl-hydroxybutyrobetaine	HMDB
L-(-)-Carnitine	HMDB
Levocarnitina	HMDB
Levocarnitinum	HMDB
R-(-)-3-Hydroxy-4-trimethylaminobutyrate	HMDB
L Carnitine	HMDB
L-Carnitine	ChEBI

Chemical Formula

C₇H₁₅NO₃

Average Molecular Weight

161.1989

Monoisotopic Molecular Weight

161.105193351

IUPAC Name

(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate

Traditional Name

L-carnitine

CAS Registry Number

541-15-1

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 Key

PHIQHXFUZVPYII-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Carnitines

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 Framework

Aliphatic acyclic compounds

External Descriptors

carnitine (CHEBI:16347 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.9	ALOGPS
logP	-4.9	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.49 m³·mol⁻¹	ChemAxon
Polarizability	16.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-1b25dacb04c3ed5be8d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9100000000-c15eaa190d1e28a4839a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-9b579c570aab7c7d3a21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ik9-0900000000-e37d3def2de1af5bd2f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ue9-8900000000-cf37f0a721cd52d86e8e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0r0c-9200000000-a11a4872036f3c33d25a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4l-9000000000-2402e260a330ff1772a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0w29-6900000000-d0136248acdd706e650b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ik9-2900000000-61732bb10307f2b183ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0zg0-9400000000-15c3db3324f1d46d3c7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ik9-2900000000-ee79f10dce9fc09246ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0900000000-3bffd5143cf8b072299e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-0900000000-e68f553bcb15d3ef5b47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-c5b43723951af6da48cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-dd1b1a023937cdcb11af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-114i-3900000000-9f24d3bc535736149e2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-632ef17d9dde38586990	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-97af6636a917c0edea61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01pc-9300000000-543e21cb6b9785149e31	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-9000000000-9128d6fe96d9c7276695	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Lung
Meat
Milk
Plasma
Serum
Synovial Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Lung	Detected but not Quantified	Not Applicable	Not Available	Porcine	23412987	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Meat	Detected and Quantified	1022.66 +/- 63.87 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	1072.83 +/- 69.97 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	829.28 +/- 38.28 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	983.18 +/- 45.99 uM	Not Available	Bovine	20831251	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	346 uM	Not Available	Bovine	20338431	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23738862	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	25087032	details
Plasma	Detected and Quantified	6.12 +/- 21.7 uM	Not Available	Bovine	25875852	details
Plasma	Detected and Quantified	0.00 +/- 0 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	1.29 +/- 0.2 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	2.54 +/- 0.51 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	3.14 +/- 0.66 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	6.34 +/- 1.87 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	6.67 +/- 2.45 uM	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24477039	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Serum	Detected and Quantified	48.251 +/- 12.9226 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	36.9763 +/- 7.0966 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	31.5666 +/- 11.4135 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	44.7269 +/- 15.9769 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	40.0263 +/- 10.8219 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	39.0586 +/- 15.3407 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.3899 +/- 12.2303 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.36 +/- 7.31 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	19.29 +/- 9.01 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	30.5504 +/- 7.1397 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	43.6222 +/- 13.5638 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	32.3627 +/- 12.6131 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	45.0218 +/- 19.1083 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.3238 +/- 10.6378 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	26.7408 +/- 9.636 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.2382 +/- 14.6668 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	46.282 +/- 15.1681 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	36.5635 +/- 15.8798 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	37.2006 +/- 11.658 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	28.6083 +/- 10.2109 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	30.3285 +/- 12.5693 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	28.4499 +/- 4.6495 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	41.6641 +/- 13.9143 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	43.7626 +/- 15.1365 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.0963 +/- 7.1923 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.2262 +/- 10.5963 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	42.2529 +/- 14.9342 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	30.2502 +/- 6.7861 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.5043 +/- 11.9146 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	52.4049 +/- 15.37 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.0364 +/- 11.6127 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	42.9042 +/- 14.4074 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	31.3116 +/- 7.0153 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	41.2464 +/- 11.4395 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details