L-CARNITINE
General Information
| Mainterm | L-CARNITINE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 541-15-1 |
| Regnum |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 10917 |
| IUPAC Name | (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate |
| InChI | 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 |
| Canonical SMILES | C[N+](C)(C)CC(CC(=O)[O-])O |
| Molecular Formula | C7H15NO3 |
| Wikipedia | levocarnitine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 161.201 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 134.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B i M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A A C A A A C B T h g A Y C C A M A A g A I A A C Q C A A A A A A A A A A A A A E I A A A C E B Q A g A A E Q A A F I A A Q A A A k A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 60.4 |
| Monoisotopic Mass | 161.105 |
| Exact Mass | 161.105 |
| XLogP3 | None |
| XLogP3-AA | -0.2 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
Toxicity Profile
| Route of Exposure | Intravenous, Oral. Absolute bioavailability is 15% (tablets or solution). Time to maximum plasma concentration was found to be 3.3 hours. |
|---|---|
| Mechanism of Toxicity | Levocarnitine can be synthesised within the body from the amino acids lysine or methionine. Vitamin C (ascorbic acid) is essential to the synthesis of carnitine. Levocarnitine is a carrier molecule in the transport of long chain fatty acids across the inner mitochondrial membrane. It also exports acyl groups from subcellular organelles and from cells to urine before they accumulate to toxic concentrations. Only the L isomer of carnitine (sometimes called vitamin BT) affects lipid metabolism. Levocarnitine is handled by several proteins in different pathways including carnitine transporters, carnitine translocases, carnitine acetyltransferases and carnitine palmitoyltransferases. |
| Metabolism | After oral administration L-carnitine which is unabsorbed is metabolized in the gastrointestinal tract by bacterial microflora. Major metabolites include trimethylamine N-oxide and [3H]-gamma-butyrobetaine. Route of Elimination: Following a single intravenous dose, 73.1 +/- 16% of the dose was excreted in the urine during the 0-24 hour interval. Post administration of oral carnitine supplements, in addition to a high carnitine diet, 58-65% of the administered radioactive dose was recovered from urine and feces in 5-11 days. Half Life: 17.4 hours (elimination) following a single intravenous dose. |
| Toxicity Values | LD<sub>50</sub> > 8g/kg (mouse, oral). |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Quaternary ammonium salts |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Carnitines |
| Alternative Parents |
|
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine. |
From ClassyFire
Targets
- General Function:
- Symporter activity
- Specific Function:
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
- Gene Name:
- SLC22A5
- Uniprot ID:
- O76082
- Molecular Weight:
- 62751.08 Da
References
- Todesco L, Bodmer M, Vonwil K, Haussinger D, Krahenbuhl S: Interaction between pivaloylcarnitine and L-carnitine transport into L6 cells overexpressing hOCTN2. Chem Biol Interact. 2009 Aug 14;180(3):472-7. doi: 10.1016/j.cbi.2009.02.014. Epub 2009 Mar 11. [19539806 ]
- General Function:
- Receptor binding
- 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:
- 70857.055 Da
References
- Cordente AG, Lopez-Vinas E, Vazquez MI, Swiegers JH, Pretorius IS, Gomez-Puertas P, Hegardt FG, Asins G, Serra D: Redesign of carnitine acetyltransferase specificity by protein engineering. J Biol Chem. 2004 Aug 6;279(32):33899-908. Epub 2004 May 21. [15155769 ]
- General Function:
- Carnitine o-palmitoyltransferase activity
- Specific Function:
- Catalyzes the transfer of the acyl group of long-chain fatty acid-CoA conjugates onto carnitine, an essential step for the mitochondrial uptake of long-chain fatty acids and their subsequent beta-oxidation in the mitochondrion. Plays an important role in triglyceride metabolism.
- Gene Name:
- CPT1A
- Uniprot ID:
- P50416
- Molecular Weight:
- 88366.92 Da
References
- Shin ES, Cho SY, Lee EH, Lee SJ, Chang IS, Lee TR: Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine. Eur J Nutr. 2006 Mar;45(3):159-64. Epub 2005 Dec 20. [16362726 ]
- General Function:
- Carnitine o-palmitoyltransferase activity
- Gene Name:
- CPT2
- Uniprot ID:
- P23786
- Molecular Weight:
- 73776.335 Da
References
- Lehtihet M, Welsh N, Berggren PO, Cook GA, Sjoholm A: Glibenclamide inhibits islet carnitine palmitoyltransferase 1 activity, leading to PKC-dependent insulin exocytosis. Am J Physiol Endocrinol Metab. 2003 Aug;285(2):E438-46. Epub 2003 Apr 8. [12684219 ]
- General Function:
- Symporter activity
- Specific Function:
- Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
- Gene Name:
- SLC22A4
- Uniprot ID:
- Q9H015
- Molecular Weight:
- 62154.48 Da
References
- Lash LH, Putt DA, Cai H: Membrane transport function in primary cultures of human proximal tubular cells. Toxicology. 2006 Dec 7;228(2-3):200-18. Epub 2006 Sep 1. [16997449 ]
- 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 Da
References
- Tonazzi A, Giangregorio N, Indiveri C, Palmieri F: Identification by site-directed mutagenesis and chemical modification of three vicinal cysteine residues in rat mitochondrial carnitine/acylcarnitine transporter. J Biol Chem. 2005 May 20;280(20):19607-12. Epub 2005 Mar 9. [15757911 ]
- General Function:
- Receptor binding
- Specific Function:
- Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
- Gene Name:
- CROT
- Uniprot ID:
- Q9UKG9
- Molecular Weight:
- 70177.935 Da
References
- Cordente AG, Lopez-Vinas E, Vazquez MI, Gomez-Puertas P, Asins G, Serra D, Hegardt FG: Mutagenesis of specific amino acids converts carnitine acetyltransferase into carnitine palmitoyltransferase. Biochemistry. 2006 May 16;45(19):6133-41. [16681386 ]
- General Function:
- Acyl carnitine transmembrane transporter activity
- Specific Function:
- Transports arginine, lysine, homoarginine, methylarginine and, to a much lesser extent, ornithine and histidine. Does not transport carnitine nor acylcarnitines. Functions by both counter-exchange and uniport mechanisms.
- Gene Name:
- SLC25A29
- Uniprot ID:
- Q8N8R3
- Molecular Weight:
- 32061.87 Da
References
- Sekoguchi E, Sato N, Yasui A, Fukada S, Nimura Y, Aburatani H, Ikeda K, Matsuura A: A novel mitochondrial carnitine-acylcarnitine translocase induced by partial hepatectomy and fasting. J Biol Chem. 2003 Oct 3;278(40):38796-802. Epub 2003 Jul 25. [12882971 ]
- General Function:
- Peroxidase activity
- Specific Function:
- Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
- Gene Name:
- MPO
- Uniprot ID:
- P05164
- Molecular Weight:
- 83867.71 Da
References
- Derin N, Agac A, Bayram Z, Asar M, Izgut-Uysal VN: Effects of L-carnitine on neutrophil-mediated ischemia-reperfusion injury in rat stomach. Cell Biochem Funct. 2006 Sep-Oct;24(5):437-42. [16130180 ]
- General Function:
- Organic cation transmembrane transporter activity
- 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.
- Gene Name:
- SLC22A16
- Uniprot ID:
- Q86VW1
- Molecular Weight:
- 64613.58 Da
References
- Enomoto A, Wempe MF, Tsuchida H, Shin HJ, Cha SH, Anzai N, Goto A, Sakamoto A, Niwa T, Kanai Y, Anders MW, Endou H: Molecular identification of a novel carnitine transporter specific to human testis. Insights into the mechanism of carnitine recognition. J Biol Chem. 2002 Sep 27;277(39):36262-71. Epub 2002 Jun 27. [12089149 ]
- General Function:
- Triglyceride lipase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
- Gene Name:
- CES1
- Uniprot ID:
- P23141
- Molecular Weight:
- 62520.62 Da
References
- Bell FP: Carnitine ester hydrolysis in arteries from normal and cholesterol-fed rabbits and the effects of carnitine esters on arterial microsomal ACAT. Comp Biochem Physiol B. 1984;79(2):125-8. [6509906 ]
- General Function:
- Xanthine oxidase activity
- Specific Function:
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
- Gene Name:
- XDH
- Uniprot ID:
- P47989
- Molecular Weight:
- 146422.99 Da
References
- Di Giacomo C, Latteri F, Fichera C, Sorrenti V, Campisi A, Castorina C, Russo A, Pinturo R, Vanella A: Effect of acetyl-L-carnitine on lipid peroxidation and xanthine oxidase activity in rat skeletal muscle. Neurochem Res. 1993 Nov;18(11):1157-62. [8255367 ]
From T3DB