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Identification
YMDB IDYMDB01534
NameHexadecanoylcarnitine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionHexadecanoylcarnitine (palmitoylcarnitine) is a long-chain fatty acid ester of carnitine with palmitoleic acid. Carnitine is used for the transport of fatty acids during beta-oxidation, during what fatty acids are broken down to acetyl-CoA. 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]
Structure
Thumb
Synonyms
  • (+)-Palmitoylcarnitine
  • (3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate
  • (3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid
  • (3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate
  • (3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid
  • (3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoate
  • (3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoic acid
  • (3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoate
  • (3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid
  • 3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium
  • D-Palmitylcarnitine
  • Hexadecanoyl-L-carnitine
  • Hexadecanoylcarnitine
  • Hexadecenoyl carnitine
  • L-Carnitine palmitoyl ester
  • L-Palmitoyl-L-carnitine
  • L-Palmitoylcarnitine
  • L(-)-Palmitylcarnitine
  • O-Hexadecanoyl-(R)-carnitine
  • O-Hexadecanoyl-R-carnitine
  • Palmitoyl D-carnitine
  • Palmitoyl-(-)-carnitine
  • Palmitoyl-L-carnitine
  • Palmityl-L-carnitine
  • Palmitylcarnitine
  • Palmitoylcarnitine
CAS number18877-64-0
WeightAverage: 399.6077
Monoisotopic: 399.334858933
InChI KeyXOMRRQXKHMYMOC-OAQYLSRUSA-N
InChIInChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1
IUPAC Name(3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Namepalmitoylcarnitine
Chemical FormulaC23H45NO4
SMILESCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
logP1.77ALOGPS
logP2.03ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity137.08 m³·mol⁻¹ChemAxon
Polarizability50.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
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 ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.4 ± 0.0 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17490
HMDB IDHMDB00222
Pubchem Compound ID11953816
Kegg IDC02990
ChemSpider ID10128117
FOODB IDFDB021910
Wikipedia IDPalmitoylcarnitine
BioCyc IDCPD-419

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
Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.
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.