Livestock Metabolome Database: Showing metabocard for Oleoylcarnitine (LMDB00461)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:50:22 UTC

Update Date

2016-07-20 20:53:42 UTC

Lmdb

LMDB00461

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oleoylcarnitine

Description

Oleoylcarnitine 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. Based on a literature review a significant number of articles have been published on Oleoylcarnitine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(9Z)-Octadecenoyl-L-carnitine	ChEBI
(R)-[(9Z)-Octadecenoyl]carnitine	ChEBI
Acylcarnitine C18:1	ChEBI
O-(9Z)-Octadecenoyl-(R)-carnitine	ChEBI
Oleoyl-L-carnitine	ChEBI
(Z)-(+-)-3-Carboxy-N,N,N-trimethyl-2-((1-oxo-9-octadecenyl)oxy)-1-propanaminium	HMDB
Oleoylcarnitine, (R-(Z))-isomer	HMDB
O-Oleoylcarnitine	HMDB
(9Z)-Octadec-9-enoylcarnitine	HMDB
cis-9-Octadecenoylcarnitine	HMDB
(R)-Oleoylcarnitine	HMDB
Oleoylcarnitine	ChEBI

Chemical Formula

C₂₅H₄₇NO₄

Average Molecular Weight

425.645

Monoisotopic Molecular Weight

425.350508997

IUPAC Name

(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

38677-66-6

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]([N+](C)(C)C)CCC([O-])=O

InChI Identifier

InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(26(2,3)4)21-22-24(27)28/h12-13,23H,5-11,14-22H2,1-4H3/b13-12-/t23-/m0/s1

InChI Key

ASTZXVSQSSBFOS-FRHQNKJESA-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:84651 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	2.02	ALOGPS
logP	2.56	ChemAxon
logS	-7.9	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	21	ChemAxon
Refractivity	147.4 m³·mol⁻¹	ChemAxon
Polarizability	53.07 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-c76c8c1a67e6b24de5c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-9000500000-4902a8769b2895518a15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	5409465	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected and Quantified	24 mol/100 mol	Not Available	Bovine	1779072	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	5409465	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Ruminal Fluid	Detected and Quantified	12.6 +/- 3.4 uM	Not Available	Bovine	Saleem F, Bouatra...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0005065

FooDB ID

FDB023614

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-20402

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

21403150

ChEBI ID

84651

PubChem Compound ID

46907933

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Minkler PE, Kerner J, North KN, Hoppel CL: Quantitation of long-chain acylcarnitines by HPLC/fluorescence detection: application to plasma and tissue specimens from patients with carnitine palmitoyltransferase-II deficiency. Clin Chim Acta. 2005 Feb;352(1-2):81-92. [15653102 ]

Showing metabocard for Oleoylcarnitine (LMDB00461)

Structure for LMDB00461 (Oleoylcarnitine)