Livestock Metabolome Database: Showing metabocard for Butyrylcarnitine (LMDB00374)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:25 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00374

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Butyrylcarnitine

Description

Butyrylcarnitine, also known as O-butanoylcarnitine, 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, butyrylcarnitine is considered to be a fatty ester. Based on a literature review a significant number of articles have been published on Butyrylcarnitine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoate	ChEBI
Butyryl-L-carnitine	ChEBI
L-Carnitine butyryl ester	ChEBI
N-Butyryl-L-(-)-carnitin	ChEBI
O-Butanoyl-(R)-carnitine	ChEBI
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoic acid	Generator
Butylcarnitine	HMDB
O-Butanoyl-carnitine	HMDB
O-Butanoylcarnitine	HMDB
Butyrylcarnitine	ChEBI

Chemical Formula

C₁₁H₂₁NO₄

Average Molecular Weight

231.2887

Monoisotopic Molecular Weight

231.147058165

IUPAC Name

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

Traditional Name

O-butanoylcarnitine

CAS Registry Number

25576-40-3

SMILES

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

InChI Identifier

InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3

InChI Key

QWYFHHGCZUCMBN-UHFFFAOYSA-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-butanoylcarnitine (CHEBI:21949 )
Fatty acyl carnitines (LMFA07070003 )

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	-2.1	ALOGPS
logP	-3.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.27	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	8	ChemAxon
Refractivity	81.86 m³·mol⁻¹	ChemAxon
Polarizability	24.8 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
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-9000000000-a5dda83cb139267daf89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-8390000000-ceb4241ebded9660319e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0090000000-5c14cfc2ec68c45a3c6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0090000000-ffb54886a9c9e0dd59c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-9000000000-45000c412d54fe872024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001r-6290000000-a53c2ce500986fed88fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-cf95ec9e05e8b6c1a98f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-9050000000-ebf3a8e1eb1d0ceaaeba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Serum	Detected and Quantified	0.1782 +/- 0.0528 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1825 +/- 0.0515 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2264 +/- 0.0919 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1919 +/- 0.1253 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2008 +/- 0.0727 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.16 +/- 0.06 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.1592 +/- 0.0413 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2267 +/- 0.101 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2504 +/- 0.1058 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.24 +/- 0.085 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1529 +/- 0.0347 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.1911 +/- 0.0756 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2228 +/- 0.0598 uM	Normal	Ovine	Goldansaz et al.,...	details