Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000023
Identification
Name: Carnitine
Description:Carnitine is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. In living cells, it is required for the transport of fatty acids during the breakdown of lipids (fats) for the generation of metabolic energy. Carnitine was originally found as a growth factor for mealworms and labeled vitamin Bt. Carnitine exists in two stereoisomers: Its biologically active form is L-carnitine, whereas its enantiomer, D-carnitine, is biologically inactive. Pseudomonas aeruginosa converts carnitine, via crotonobetaine, to gamma-butyrobetaine in the presence of C and N sources and under anaerobic conditions. This two-step pathway requires L-(-)-carnitine dehydratase and crotonobetaine reductase. Anaerobic carnitine metabolism in Pseudomonas aeruginosa involves six genes organized in the cai operon and located at the first minute on the Pseudomonas aeruginosa chromosome.
Structure
Thumb
Synonyms:
  • γ-Trimethyl-hydroxybutyrobetaine
  • (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate
  • (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyric acid
  • (-)-Carnitine
  • (-)-L-Carnitine
  • (3-carboxy-2-hydroxypropyl)trimethyl-Ammonium hydroxide inner salt
  • (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide
  • (R)-Carnitine
  • (S)-carnitine
  • 1-carnitine
  • 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium
  • 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-Propanaminium hydroxide inner salt
  • 3-Hydroxy-4-trimethylammoniobutanoate
  • 3-Hydroxy-4-trimethylammoniobutanoic acid
  • Bicarnesine
  • Carniking
  • Carniking 50
  • Carnilean
  • Carnipass
  • Carnipass 20
  • Carnitene
  • Carnitine (L-form)
  • Carnitor
  • Carnitor, Levocarnitine
  • D-carnitine
  • Delta-carnitine
  • Dl-carnitine
  • g-Trimethyl-ammonium-b-hydroxybutirate
  • g-Trimethyl-ammonium-b-hydroxybutiric acid
  • g-Trimethyl-b-hydroxybutyrobetaine
  • g-Trimethyl-hydroxybutyrobetaine
  • Gamma-trimethyl-ammonium-beta-hydroxybutirate
  • gamma-Trimethyl-ammonium-beta-hydroxybutiric acid
  • Gamma-trimethyl-beta-hydroxybutyrobetaine
  • Gamma-Trimethyl-hydroxybutyrobetaine
  • Karnitin
  • L-γ-trimethyl-β-hydroxybutyrobetaine
  • L-(-)-Carnitine
  • L-Carnitine
  • L-g-Trimethyl-b-hydroxybutyrobetaine
  • L-gamma-Trimethyl-beta-hydroxybutyrobetaine
  • L-γ-Trimethyl-β-hydroxybutyrobetaine
  • Levocarnitina
  • Levocarnitine
  • Levocarnitine chloride
  • Levocarnitinum
  • R-(-)-3-Hydroxy-4-trimethylaminobutyrate
  • R-(-)-3-Hydroxy-4-trimethylaminobutyric acid
  • Vitamin B T
  • Vitamin Bt
  • γ-Trimethyl-ammonium-β-hydroxybutirate
  • γ-Trimethyl-ammonium-β-hydroxybutiric acid
  • γ-Trimethyl-hydroxybutyrobetaine
  • γ-Trimethyl-β-hydroxybutyrobetaine
  • δ-Carnitine
Chemical Formula: C7H16NO3
Average Molecular Weight: 162.2068
Monoisotopic Molecular Weight: 162.113018383
InChI Key: PHIQHXFUZVPYII-UHFFFAOYSA-O
InChI:InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/p+1
CAS number: 541-15-1
IUPAC Name:(3-carboxy-2-hydroxypropyl)trimethylazanium
Traditional IUPAC Name: (+-)-carnitine
SMILES:C[N+](C)(C)CC(O)CC(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Choline
  • Beta-hydroxy acid
  • Hydroxy acid
  • Quaternary ammonium salt
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: 210-212 °C
Experimental Properties:
PropertyValueSource
Water Solubility:2500.0 mg/mlPhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.58 mg/mLALOGPS
logP-2.8ALOGPS
logP-4.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.65 m3·mol-1ChemAxon
Polarizability17.18 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
References
References:
  • Canovas, M., Bernal, V., Sevilla, A., Iborra, J. L. (2007). "Salt stress effects on the central and carnitine metabolisms of Escherichia coli." Biotechnol Bioeng 96:722-737. Pubmed: 16894634
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17126
HMDB IDHMDB00062
Pubchem Compound ID10917
Kegg IDC00487
ChemSpider ID83
WikipediaL-Carnitine
BioCyc IDCARNITINE
EcoCyc IDCARNITINE

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proV
Locus Tag:
PA5094
Molecular weight:
30.7 kDa

Transporters