Bovine Metabolome Database: Showing metabocard for Butyrylcarnitine (BMDB0002013)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:49:55 UTC

Update Date

2020-06-04 20:04:02 UTC

BMDB ID

BMDB0002013

Secondary Accession Numbers

BMDB02013

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

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

231.292

Monoisotopic Molecular Weight

231.14705816

IUPAC Name

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

Traditional Name

O-butanoylcarnitine

CAS Registry Number

25576-40-3

SMILES

CCCC(=O)O[C@H](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/t9-/m1/s1

InChI Key

QWYFHHGCZUCMBN-SECBINFHSA-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

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	-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

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	0.2 +/- 0.1 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
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected and Quantified	0.36 +/- 0.08 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	16 +/- 6 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Characterization ...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	4.4 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	5.8 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	6.6 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	3.99 +/- 0.04 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	0.05 +/- 0.02 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	22 +/- 8 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	2.8 +/- 0.7 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002013

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6436

PubChem Compound

213144

PDB ID

Not Available

ChEBI ID

21949

References

Synthesis Reference

Lozano Pedro; Daz Mirta; de Diego Teresa; Iborra Jose L Ester synthesis from trimethylammonium alcohols in dry organic media catalyzed by immobilized Candida antarctica lipase B. Biotechnology and bioengineering (2003), 82(3), 352-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals (2009). Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics.
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 Butyrylcarnitine (BMDB0002013)

Structure for BMDB0002013 (Butyrylcarnitine)