ChemFOnt: Showing chemical card for Malonylcarnitine (CFc000001406)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:02 UTC

Chemfont ID

CFc000001406

Molecule Identification

Common Name

Malonylcarnitine

Definition

Malonylcarnitine is a metabolite that accumulates with specific disruption of fatty-acid oxidation caused by the impaired entry of long-chain acylcarnitine esters into the mitochondria and failure of the mitochondrial respiratory chain at complex 11 and malonyl-CoA decarboxylase (EC 4.1.1.9) deficiency (OMIM: 248360 ). Malonylcarnitine has also been found to accumulate in some newborns with medium-chain acyl-CoA dehydrogenase (EC 1.3.99.3) deficiency (OMIM: 201450 ). (PMID:11558490 , 15303003 , 12651823 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-[(2-Carboxyacetyl)oxy]-4-hydroxy-N,N,N-trimethyl-4-oxo-1-butanaminium inner salt	HMDB
3-Carboxy-2-[(carboxyacetyl)oxy]-N,N,N-trimethyl-1-propanaminium inner salt	HMDB
Malonyl-L-carnitine	HMDB

Chemical Formula

C₁₀H₁₇NO₆

Average Molecular Weight

247.2451

Monoisotopic Molecular Weight

247.105587281

IUPAC Name

(3S)-3-[(2-carboxyacetyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-[(2-carboxyacetyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

910825-21-7

SMILES

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

InChI Identifier

InChI=1S/C10H17NO6/c1-11(2,3)6-7(4-8(12)13)17-10(16)5-9(14)15/h7H,4-6H2,1-3H3,(H-,12,13,14,15)/t7-/m0/s1

InChI Key

ZGNBLKBZJBJFDG-ZETCQYMHSA-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
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-D-carnitine (CHEBI:86047 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11558490)

Organ

Placenta (HMDB: HMDB0002095)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Cellular substructure

Extracellular (HMDB: HMDB0002095)
Membrane (HMDB: HMDB0002095)

Source

Exogenous

Exogenous (HMDB: HMDB0002095)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002095)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Pregnancy (MarkerDB: MDB00000376)
Malonyl Co A Decarboxylase Deficiency (MarkerDB: MDB00000376)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.6	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.98 m³·mol⁻¹	ChemAxon
Polarizability	23.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022843

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833583

PDB ID

Not Available

ChEBI ID

86047

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Malonylcarnitine (CFc000001406)

MOL for CFc000001406 (Malonylcarnitine)

3D MOL for CFc000001406 (Malonylcarnitine)

3D SDF for CFc000001406 (Malonylcarnitine)

3D-SDF for CFc000001406 (Malonylcarnitine)

PDB for CFc000001406 (Malonylcarnitine)

3D PDB for CFc000001406 (Malonylcarnitine)

SMILES for CFc000001406 (Malonylcarnitine)

INCHI for CFc000001406 (Malonylcarnitine)

Structure for CFc000001406 (Malonylcarnitine)

3D Structure for CFc000001406 (Malonylcarnitine)