Record Information
Version2.0
Creation Date2012-05-31 09:56:31 -0600
Update Date2015-09-13 12:56:05 -0600
Secondary Accession Numbers
  • ECMDB00062
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. E. coli 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 Escherichia coli involves six genes organized in the cai operon and located at the first minute on the E. coli 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
Weight:Average: 162.2068
Monoisotopic: 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
DescriptionThis compound belongs to the class of chemical entities known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentCarnitines
Alternative Parents
Substituents
  • Carnitine
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Fatty acid
  • Hydroxy acid
  • Tetraalkylammonium salt
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
4± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:Not Available
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
Uniprot ID:
P14175
Molecular weight:
44162
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible transfer of the CoA moiety from gamma-butyrobetainyl-CoA to L-carnitine to generate L-carnitinyl- CoA and gamma-butyrobetaine. Is also able to catalyze the reversible transfer of the CoA moiety from gamma-butyrobetainyl- CoA or L-carnitinyl-CoA to crotonobetaine to generate crotonobetainyl-CoA
Gene Name:
caiB
Uniprot ID:
P31572
Molecular weight:
45126
General function:
Involved in transporter activity
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proW
Uniprot ID:
P14176
Molecular weight:
37619
General function:
Involved in catalytic activity
Specific function:
Could catalyze the transfer of CoA to carnitine, generating the initial carnitinyl-CoA needed for the CaiB reaction cycle
Gene Name:
caiC
Uniprot ID:
P31552
Molecular weight:
58559
General function:
Involved in transporter activity
Specific function:
Member of a multicomponent binding-protein-dependent transport system (the proU transporter) which serves as the glycine betaine/L-proline transporter
Gene Name:
proX
Uniprot ID:
P0AFM2
Molecular weight:
36022

Transporters

General function:
Involved in transporter activity
Specific function:
Proton symporter that senses osmotic shifts and responds by importing osmolytes such as proline, glycine betaine, stachydrine, pipecolic acid, ectoine and taurine. It is both an osmosensor and an osmoregulator which is available to participate early in the bacterial osmoregulatory response
Gene Name:
proP
Uniprot ID:
P0C0L7
Molecular weight:
54845
General function:
Involved in transporter activity
Specific function:
Involved in a multicomponent binding-protein-dependent transport system for glycine betaine/L-proline
Gene Name:
proW
Uniprot ID:
P14176
Molecular weight:
37619
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
Catalyzes the exchange of L-carnitine for gamma- butyrobetaine and related betaines
Gene Name:
caiT
Uniprot ID:
P31553
Molecular weight:
56587
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368