CHEBI:17126 - carnitine

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ChEBI Name carnitine ChEBI ID CHEBI:17126 Definition An amino-acid betaine that is butanoate substituted with a hydroxy group at position C-3 and a trimethylammonium group at C-4. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:11817, CHEBI:13947, CHEBI:23038, CHEBI:20047, CHEBI:29085 Supplier Information ChemicalBook:CB41124723, ChemicalBook:CB8400042, ChemicalBook:CB1400043, eMolecules:901780 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Carnitine is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria. In support of energy metabolism, carnitine transports long-chain fatty acids from the cytosol into mitochondria to be oxidized for free energy production, and also participates in removing products of metabolism from cells. Given its key metabolic roles, carnitine is concentrated in tissues like skeletal and cardiac muscle that metabolize fatty acids as an energy source. Generally individuals, including strict vegetarians, synthesize enough L-carnitine in vivo. Carnitine exists as one of two stereoisomers: the two enantiomers d-carnitine (S-(+)-) and l-carnitine (R-(−)-). Both are biologically active, but only l-carnitine naturally occurs in animals, and d-carnitine is toxic as it inhibits the activity of the l-form. At room temperature, pure carnitine is a whiteish powder, and a water-soluble zwitterion with relatively low toxicity. Derived from amino acids, carnitine was first extracted from meat extracts in 1905, leading to its name from Latin, "caro/carnis" or flesh. Some individuals with genetic or medical disorders (such as preterm infants) cannot make enough carnitine, requiring dietary supplementation. Despite common carnitine supplement consumption among athletes for improved exercise performance or recovery, there is insufficient high-quality clinical evidence to indicate it provides any benefit. Read full article at Wikipedia Formula C7H15NO3 Net Charge 0 Average Mass 161.19894 Monoisotopic Mass 161.10519 InChI InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3 InChIKey PHIQHXFUZVPYII-UHFFFAOYSA-N SMILES C[N+](C)(C)CC(O)CC([O-])=O Metabolite of Species Details Mus musculus (NCBI:txid10090) See: PubMed Homo sapiens (NCBI:txid9606) See: PubMed Roles Classification Biological Role(s): mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). View more via ChEBI Ontology ChEBI Ontology Outgoing carnitine (CHEBI:17126) has functional parent butyrate (CHEBI:17968) carnitine (CHEBI:17126) has role human metabolite (CHEBI:77746) carnitine (CHEBI:17126) has role mouse metabolite (CHEBI:75771) carnitine (CHEBI:17126) is a amino-acid betaine (CHEBI:22860) carnitine (CHEBI:17126) is conjugate base of carnitinium (CHEBI:3424) Incoming (11Z)-eicoseneoylcarnitine (CHEBI:73118) has functional parent carnitine (CHEBI:17126) (11Z,14Z)-eicosadienoylcarnitine (CHEBI:73119) has functional parent carnitine (CHEBI:17126) (13Z,16Z)-docosadienoylcarnitine (CHEBI:73120) has functional parent carnitine (CHEBI:17126) (2E)-7-carboxyhept-2-enoylcarnitine (CHEBI:73050) has functional parent carnitine (CHEBI:17126) (2E)-octenoylcarnitine (CHEBI:73037) has functional parent carnitine (CHEBI:17126) (2E,4Z)-decadienoylcarnitine (CHEBI:73047) has functional parent carnitine (CHEBI:17126) (2E,5Z,7E)-decatrienoylcarnitine (CHEBI:73046) has functional parent carnitine (CHEBI:17126) (5Z)-13-carboxytridec-5-enoylcarnitine (CHEBI:73069) has functional parent carnitine (CHEBI:17126) (7Z,10Z,13Z,16Z)-docosatetraenoylcarnitine (CHEBI:73122) has functional parent carnitine (CHEBI:17126) (9Z)-3-hydroxydodecenoylcarnitine (CHEBI:73106) has functional parent carnitine (CHEBI:17126) (9Z)-3-hydroxyoctadecenoylcarnitine (CHEBI:73076) has functional parent carnitine (CHEBI:17126) (9Z,12Z,15Z)-3-hydroxyoctadecatrienoylcarnitine (CHEBI:73116) has functional parent carnitine (CHEBI:17126) 2-ethylacryloylcarnitine (CHEBI:71180) has functional parent carnitine (CHEBI:17126) 3-hydroxy-cis-5-octenoylcarnitine (CHEBI:73043) has functional parent carnitine (CHEBI:17126) 3-hydroxyarachidonoylcarnitine (CHEBI:73101) has functional parent carnitine (CHEBI:17126) 3-hydroxybutyrylcarnitine (CHEBI:72995) has functional parent carnitine (CHEBI:17126) 3-hydroxydecanoylcarnitine (CHEBI:73051) has functional parent carnitine (CHEBI:17126) 3-hydroxydodecanoylcarnitine (CHEBI:73056) has functional parent carnitine (CHEBI:17126) 3-hydroxyeicosanoylcarnitine (CHEBI:73103) has functional parent carnitine (CHEBI:17126) 3-hydroxyhexadecanoylcarnitine (CHEBI:73070) has functional parent carnitine (CHEBI:17126) 3-hydroxylinoleoylcarnitine (CHEBI:73075) has functional parent carnitine (CHEBI:17126) 3-hydroxyoctadecanoylcarnitine (CHEBI:73077) has functional parent carnitine (CHEBI:17126) 3-hydroxytetradecanoylcarnitine (CHEBI:73063) has functional parent carnitine (CHEBI:17126) O-(11-carboxyundecanoyl)carnitine (CHEBI:73064) has functional parent carnitine (CHEBI:17126) O-(13-carboxytridecanoyl)carnitine (CHEBI:73071) has functional parent carnitine (CHEBI:17126) O-(17-carboxyheptadecanoyl)carnitine (CHEBI:73104) has functional parent carnitine (CHEBI:17126) O-(4,8-dimethylnonanoyl)carnitine (CHEBI:63874) has functional parent carnitine (CHEBI:17126) O-[(2E)-hexenedioyl]carnitine (CHEBI:73042) has functional parent carnitine (CHEBI:17126) O-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]carnitine (CHEBI:73123) has functional parent carnitine (CHEBI:17126) O-[(9Z)-17-carboxyheptadec-9-enoyl]carnitine (CHEBI:73102) has functional parent carnitine (CHEBI:17126) O-acetyl-L-carnitine (CHEBI:57589) has functional parent carnitine (CHEBI:17126) O-acylcarnitine (CHEBI:17387) has functional parent carnitine (CHEBI:17126) O-arachidonoylcarnitine (CHEBI:73082) has functional parent carnitine (CHEBI:17126) O-behenoylcarnitine (CHEBI:73105) has functional parent carnitine (CHEBI:17126) O-icosanoylcarnitine (CHEBI:73100) has functional parent carnitine (CHEBI:17126) O-linoleoylcarnitine (CHEBI:73072) has functional parent carnitine (CHEBI:17126) O-methylmalonylcarnitine (CHEBI:73031) has functional parent carnitine (CHEBI:17126) O-palmitoleoylcarnitine (CHEBI:73066) has functional parent carnitine (CHEBI:17126) O-pimeloylcarnitine (CHEBI:73049) has functional parent carnitine (CHEBI:17126) O-sebacoylcarnitine (CHEBI:73057) has functional parent carnitine (CHEBI:17126) O-succinylcarnitine (CHEBI:73034) has functional parent carnitine (CHEBI:17126) (R)-carnitine (CHEBI:16347) is a carnitine (CHEBI:17126) (S)-carnitine (CHEBI:11060) is a carnitine (CHEBI:17126) L-carnitine-d9 (CHEBI:191945) is a carnitine (CHEBI:17126) carnitinium (CHEBI:3424) is conjugate acid of carnitine (CHEBI:17126) IUPAC Name 3-hydroxy-4-(trimethylammonio)butanoate Synonyms Sources carnitine UniProt D,L-carnitine MetaCyc Manual Xrefs Databases C00487 KEGG COMPOUND Carnitine Wikipedia DB02648 DrugBank DL-CARNITINE MetaCyc US4255449 Patent US4315944 Patent View more database links Registry Numbers Types Sources 1866665 Reaxys Registry Number Reaxys 461-06-3 CAS Registry Number ChemIDplus Citations Last Modified 11 November 2014