Bovine Metabolome Database: Showing metabocard for cis-5-Tetradecenoylcarnitine (BMDB0002014)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:49:56 UTC

Update Date

2020-06-04 19:15:37 UTC

BMDB ID

BMDB0002014

Secondary Accession Numbers

BMDB02014

Metabolite Identification

Common Name

cis-5-Tetradecenoylcarnitine

Description

Tetradecenoylcarnitine 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, tetradecenoylcarnitine is considered to be a fatty ester lipid molecule. Tetradecenoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetradecenoylcarnitine exists in all eukaryotes, ranging from yeast to humans. Tetradecenoylcarnitine has been found to be associated with several diseases known as obesity and eosinophilic esophagitis; also tetradecenoylcarnitine has been linked to the inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoate	ChEBI
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoic acid	Generator
cis-5-Tetradecenoylcarnitine	ChEBI

Chemical Formula

C₂₁H₃₉NO₄

Average Molecular Weight

369.5387

Monoisotopic Molecular Weight

369.287908741

IUPAC Name

3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

cis-5-tetradecenoylcarnitine

CAS Registry Number

835598-21-5

SMILES

CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3/b13-12-

InChI Key

NNCBVXBBLABOCB-SEYXRHQNSA-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-acylcarnitine (CHEBI:73060 )

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	0.48	ALOGPS
logP	0.78	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	4.24	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	17	ChemAxon
Refractivity	128.99 m³·mol⁻¹	ChemAxon
Polarizability	44.6 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-9210000000-d55933555203a81af3b0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fkc-0729000000-b7724178fd672abeda7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1900000000-a2f60fad8c99a570c7b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02fx-4900000000-6ae1e898595b8e8b61f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0029000000-a5108e2a8a5c949c7942	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-1289000000-351e00d1ad0b6a3015e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-7590000000-8eeb0dac52aa2c1d6246	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-1a5965dc435463ee085f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-9005000000-84dcf946c3b41ee8ec83	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
Liver
Longissimus Thoracis Muscle
Milk
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	0.0518 +/- 0.0103 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Liver	Detected and Quantified	0.011 +/- 0.002 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.01 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.021 +/- 0.001 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.032 +/- 0.002 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.047 +/- 0.003 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Ruminal Fluid	Detected and Quantified	0.007 +/- 0.002 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	0.09 +/- 0.001 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semimembranosus Muscle	Detected and Quantified	0.01 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.011 +/- 0.003 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002014

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022796

KNApSAcK ID

Not Available

Chemspider ID

17216151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6437

PubChem Compound

22833575

PDB ID

Not Available

ChEBI ID

73060

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 cis-5-Tetradecenoylcarnitine (BMDB0002014)

Structure for BMDB0002014 (cis-5-Tetradecenoylcarnitine)