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Identification
YMDB IDYMDB00616
Name(R)-Carnitine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCarnitine is a quaternary ammonium ubiquitous compound biosynthetized from the amino acids lysine and methionine and involved in the transport of long-chain fatty acids to be used in fatty acid metabolism. 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
Synonyms
  • (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate
  • (-)-carnitine
  • (-)-L-Carnitin
  • (-)-L-Carnitine
  • (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide
  • (R)-Carnitine
  • (s)-carnitine
  • 1-carnitine
  • 3-carboxy-2-hydroxy-n
  • 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
  • Levocarnitine
  • Levocarnitinum
  • n-trimethyl-1-propanaminium
  • R-(-)-3-hydroxy-4-trimethylaminobutyrate
  • vitamin bt
  • 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt
  • Carnicor
  • L-g-Trimethyl-b-hydroxybutyrobetaine
  • L-Γ-trimethyl-β-hydroxybutyrobetaine
  • Carniking
  • Carniking 50
  • Carnipass
  • Carnipass 20
  • Levocarnitina
  • L Carnitine
CAS number541-15-1
WeightAverage: 161.1989
Monoisotopic: 161.105193351
InChI KeyPHIQHXFUZVPYII-ZCFIWIBFSA-N
InChIInChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1
IUPAC Name(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Traditional IUPAC NameL-carnitine
Chemical FormulaC7H15NO3
SMILESC[N+](C)(C)C[C@H](O)CC([O-])=O
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
Polarizability16.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid metabolismec00071 Map00071
SMPDB Reactions
Palmityl-CoA + (R)-CarnitineHexadecanoylcarnitine + Coenzyme A
KEGG Reactions
(R)-Carnitine + Acetyl-CoAO-acetylcarnitinium + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16347
HMDB IDHMDB00062
Pubchem Compound ID10917
Kegg IDC00318
ChemSpider ID10455
FOODB IDFDB000572
WikipediaCarnitine
BioCyc IDCARNITINE

Enzymes

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
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x43deed4>
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
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x43bf2dc>
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
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x43aa0d0>

Transporters

General function:
Involved in transport
Specific function:
General amino acid permease with broad substrate specificity. Can also transport carnitine
Gene Name:
AGP2
Uniprot ID:
P38090
Molecular weight:
67261.29688
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x43861bc>
General function:
Involved in binding
Specific function:
Transports carnitine, acetylcarnitine, propionylcarnitine and to a much lower extent medium- and long- chain acylcarnitines
Gene Name:
CRC1
Uniprot ID:
Q12289
Molecular weight:
34753.89844
Reactions
#<Reaction::ActiveRecord_Associations_CollectionProxy:0x4379624>