L-Carnitine (YMDB00188)

Identification
YMDB IDYMDB00188
NameL-Carnitine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCarnitine is an ubiquitous compound biosynthetised from the amino acids lysine and methionine and involved in the transport of long-chain fatty acids. The active form is L-carnitine whereas D-carnitine is biologically inactive. Fatty acids are broken down to acetyl-CoA through beta-oxidation, which in yeast takes place exclusively in peroxisomes. Acetyl-CoA is then used in the glyoxylate cycle for gluconeogenesis and formation of carbohydrates, or transported to mitochondrion for the generation of metabolic energy through the citric acid cycle. [Biocyc PWY-6111] [PMID: 10545096]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate
  • (-)-carnitine
  • (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide
  • (r)-carnitine
  • (s)-carnitine
  • 1-carnitine
  • 3-carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium
  • 3-hydroxy-4-trimethylammoniobutanoate
  • 3-hydroxy-4-trimethylammoniobutanoic acid
  • Bicarnesine
  • Carnilean
  • Carnitene
  • Carnitine
  • Carnitor
  • D-carnitine
  • delta-carnitine
  • DL-carnitine
  • Gamma-trimethyl-ammonium-beta-hydroxybutirate
  • Gamma-trimethyl-beta-hydroxybutyrobetaine
  • Gamma-trimethyl-hydroxybutyrobetaine
  • Karnitin
  • L-(-)-carnitine
  • L-carnitine
  • L-gamma-trimethyl-beta-hydroxybutyrobetaine
  • Levocarnitina
  • Levocarnitine
  • Levocarnitinum
  • R-(-)-3-hydroxy-4-trimethylaminobutyrate
  • Vitamin BT
  • (+)-Carnitine
  • Carnitine D-form
  • D-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide, inner salt
CAS number541-15-1
WeightAverage: 161.1989
Monoisotopic: 161.105193351
InChI KeyPHIQHXFUZVPYII-LURJTMIESA-N
InChIInChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m0/s1
IUPAC Name(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name(+)-carnitine
Chemical FormulaC7H15NO3
SMILES[H]O[C@@]([H])(C([H])([H])C([O-])=O)C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentCarnitines
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point197 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.33 g/LALOGPS
logP-2.9ALOGPS
logP-4.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.49 m³·mol⁻¹ChemAxon
Polarizability16.76 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Extracellular, Mitochondrion, Peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid metabolismec00071 Map00071
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9100000000-1b25dacb04c3ed5be8d0JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-2900000000-838e3352a967414a72b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0pbl-9200000000-00392257546f220a99e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-9000000000-f740371c8e6547d00caaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0900000000-c58323e2e9eb0d43afd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03di-0900000000-07916b6c77becc7b8c81JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-3bffd5143cf8b072299eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-0900000000-e68f553bcb15d3ef5b47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-77b63d360e6d4a61dff3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-dd1b1a023937cdcb11afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-3900000000-2ec1dcd043005fc2eb27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-07d7ea1192c1873ad80dJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Synthesis Reference: Bols, Mikael; Lundt, Inge; Pedersen, Christian. Simple synthesis of (R)-carnitine from D-galactono-1,4-lactone. Tetrahedron (1992), 48(2), 319-24.
External Links:
ResourceLink
CHEBI ID11060
HMDB IDHMDB00062
Pubchem Compound ID2724480
Kegg IDC00318
ChemSpider ID2006614
FOODB IDNot Available
WikipediaCarnitine
BioCyc IDCARNITINE

Enzymes

Protein Details
1. Carnitine O-acetyltransferase, mitochondrial
General function:
Involved in acyltransferase activity
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:
CAT2
Uniprot ID:
P32796
Molecular weight:
77241.20313
Reactions
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.
Protein Details
2. Putative mitochondrial carnitine O-acetyltransferase
General function:
Involved in acyltransferase activity
Specific function:
Involved in the transfer of acetyl-CoA into mitochondria. May also be involved in the metabolism of acetate and of ethanol
Gene Name:
YAT1
Uniprot ID:
P80235
Molecular weight:
77764.79688
Reactions
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.
Protein Details
3. Carnitine O-acetyltransferase YAT2
General function:
Involved in acyltransferase activity
Specific function:
Involved in the shutteling of acetyl-CoA in the cell
Gene Name:
YAT2
Uniprot ID:
P40017
Molecular weight:
103333.0
Reactions
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.