Dodecanoylcarnitine (YMDB01529)

Identification

YMDB ID

YMDB01529

Name

Dodecanoylcarnitine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Dodecanoylcarnitine (lauroylcarnitine) is a long-chain fatty acid ester of carnitine with lauric 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

MOL SDF PDB SMILES InChI

Synonyms

(-)-Lauroylcarnitine
(R)-Dodecanoylcarnitine
Dodecanoyl-L-carnitine
L-Carnitine dodecanoyl ester
Lauroyl-L-carnitine
Lauroyl-L(-)-carnitin
Lauroyl-L(-)-carnitin [German]
Lauroylcarnitine
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoate
Laurylcarnitine
O-C12:0-L-Carnitine
O-Dodecanoyl-R-carnitine
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoic acid
C12 Carnitine
L-Lauroylcarnitine
Lauroyl-L(-)-carnitine
Dodecanoylcarnitine
O-Dodecanoylcarnitine
O-Lauroylcarnitine
O-Lauroyl-L-carnitine

CAS number

25518-54-1

Weight

Average: 343.5014
Monoisotopic: 343.272258677

InChI Key

FUJLYHJROOYKRA-QGZVFWFLSA-N

InChI

InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/t17-/m1/s1

IUPAC Name

(3R)-3-(dodecanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional IUPAC Name

lauroyl-L(-)-carnitin

Chemical Formula

C₁₉H₃₇NO₄

SMILES

CCCCCCCCCCCC(=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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl 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 Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:77086 )
O-dodecanoylcarnitine (CHEBI:77086 )
laurate ester (CHEBI:77086 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	3.8e-05 g/L	ALOGPS
logP	0.03	ALOGPS
logP	0.26	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	118.67 m³·mol⁻¹	ChemAxon
Polarizability	41.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
1 ± 0 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9300000000-0cd49618a50984aad982	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0002-0900000000-1c57ff1372236d823d80	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-9000000000-ef35ea7a4d61bac8cb20	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-ce07549e40447c69729f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9005000000-ce18984499544d19b739	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	77086
HMDB ID	HMDB02250
Pubchem Compound ID	168381
Kegg ID	Not Available
ChemSpider ID	147288
FOODB ID	FDB022928
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xa6e120c0>