Livestock Metabolome Database: Showing metabocard for Propionylcarnitine (LMDB00253)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:44 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00253

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Propionylcarnitine

Description

Propionylcarnitine is present in high abundance in the urine of patients with Methylmalonyl-CoA mutase (MUT) deficiency, (together with Methylmalonic acid). MUT is a mitochondrial enzyme that catalyzes the isomerization of methylmalonyl-CoA to succinyl-CoA (OMIM 609058 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt	ChEBI
O-Propionylcarnitine	ChEBI
Propionyl carnitine	ChEBI
(+/-)-propionylcarnitine chloride	HMDB
(3-Carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt	HMDB
L-Propionylcarnitine	HMDB
O-Propanoylcarnitine	HMDB
Propionyl-carnitine	HMDB
Propionyl-L-carnitine	HMDB
Propionylcarnitine, (+-)-isomer	HMDB
Propionylcarnitine, (R)-isomer	HMDB

Chemical Formula

C₁₀H₁₉NO₄

Average Molecular Weight

217.2622

Monoisotopic Molecular Weight

217.131408101

IUPAC Name

3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

propionyl-L-carnitine

CAS Registry Number

17298-37-2

SMILES

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

InChI Identifier

InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3

InChI Key

UFAHZIUFPNSHSL-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-acylcarnitine (CHEBI:28867 )
Fatty acyl carnitines (C03017 )

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	-2.3	ALOGPS
logP	-3.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.19	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	7	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	22.72 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

Not Available

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma
Ruminal Fluid
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	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25828073	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Plasma	Detected and Quantified	0.06 +/- 0.03 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	0.3 +/- 0.08 uM	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	0.036 +/- 0.006 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.01 +/- 0.01 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.017 +/- 0.01 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.01 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.01 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.011 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.016 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.017 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.023 uM	Not Available	Bovine	22959937	details
Serum	Detected and Quantified	0.3941 +/- 0.1082 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.5813 +/- 0.1961 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	0.7735 +/- 0.4741 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.4187 +/- 0.1842 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.6179 +/- 0.1722 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.37 +/- 0.14 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.3573 +/- 0.1044 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.8076 +/- 0.6593 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.1889 +/- 0.6187 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.9146 +/- 0.8987 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.3116 +/- 0.0902 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.5961 +/- 0.2466 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.6395 +/- 0.3282 uM	Normal	Ovine	Goldansaz et al.,...	details