Bovine Metabolome Database: Showing metabocard for Dodecanoylcarnitine (BMDB0002250)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:53:11 UTC

Update Date

2020-06-04 19:49:46 UTC

BMDB ID

BMDB0002250

Secondary Accession Numbers

BMDB02250

Metabolite Identification

Common Name

Dodecanoylcarnitine

Description

Dodecanoylcarnitine, also known as lauroylcarnitine or O-C12:0-L-carnitine, 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. Thus, dodecanoylcarnitine is considered to be a fatty ester lipid molecule. Dodecanoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dodecanoylcarnitine exists in all eukaryotes, ranging from yeast to humans. Dodecanoylcarnitine has been found to be associated with several diseases known as pregnancy and obesity; also dodecanoylcarnitine has been linked to several inborn metabolic disorders including celiac disease and very long chain acyl-coa dehydrogenase deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Lauroylcarnitine	ChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoate	ChEBI
(R)-Dodecanoylcarnitine	ChEBI
Dodecanoyl-L-carnitine	ChEBI
L-Carnitine dodecanoyl ester	ChEBI
Lauroyl-L(-)-carnitin	ChEBI
Lauroyl-L-carnitine	ChEBI
Lauroylcarnitine	ChEBI
Laurylcarnitine	ChEBI
O-C12:0-L-Carnitine	ChEBI
O-Dodecanoyl-R-carnitine	ChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoic acid	Generator
C12 Carnitine	HMDB
L-Lauroylcarnitine	HMDB
Lauroyl-L(-)-carnitine	HMDB
Dodecanoylcarnitine	HMDB
O-Dodecanoylcarnitine	ChEBI, HMDB
O-Lauroylcarnitine	ChEBI, HMDB
O-Lauroyl-L-carnitine	ChEBI, HMDB

Chemical Formula

C₁₉H₃₇NO₄

Average Molecular Weight

343.5014

Monoisotopic Molecular Weight

343.272258677

IUPAC Name

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

Traditional Name

lauroyl-L(-)-carnitin

CAS Registry Number

25518-54-1

SMILES

CCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

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

InChI Key

FUJLYHJROOYKRA-QGZVFWFLSA-N

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 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

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

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Blood
Fibroblasts
Liver
Longissimus Thoracis Muscle
Milk
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.04 +/- 0.01 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected and Quantified	0.02-0.03 uM	Not Specified	Not Specified	Normal	PMID: 28453535	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected and Quantified	0.031 +/- 0.004 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.1 +/- 0.1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	3.75 +/- 0.03 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.3 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4.43 +/- 0.04 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	3.4 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.01 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	0.04 +/- 0.03 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.04 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002250

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022928

KNApSAcK ID

C00052268

Chemspider ID

147288

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6573

PubChem Compound

168381

PDB ID

Not Available

ChEBI ID

77086

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Dodecanoylcarnitine (BMDB0002250)

Structure for BMDB0002250 (Dodecanoylcarnitine)