ChemFOnt: Showing chemical card for 4,8 Dimethylnonanoyl carnitine (CFc000002657)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:35 UTC

Chemfont ID

CFc000002657

Molecule Identification

Common Name

4,8 Dimethylnonanoyl carnitine

Definition

4,8 dimethylnonanoyl carnitine is an intermediate in phytanic and pristanic acid metabolism. Both phytanic acid and pristanic acid are initially oxidized in peroxisomes to 4,8-dimethylnonanoyl-CoA, which is then converted to to 4,8-dimethylnonanoyl carnitine (presumably by peroxisomal carnitine octanoyltransferase), and exported to the mitochondrion. After transport across the mitochondrial membrane and transfer of the acylgroup to coenzyme A, further oxidation to 2,6-dimethylheptanoyl-CoA occurs (PMID: 9469587 ). 4,8 dimethylnonanoyl carnitine is not a substrate for carnitine acetyltransferase, another acyltransferase localized in peroxisomes, which catalyzes the formation of carnitine esters of the other products of pristanic acid beta-oxidation, namely acetyl-CoA and propionyl-CoA. (PMID: 10486279 ). Earlier studies have shown that pristanic acid undergoes three cycles of beta-oxidation in peroxisomes to produce 4,8-dimethylnonanoyl-CoA (DMN-CoA) which is then transported to the mitochondria for full oxidation to CO(2) and H(2)O. In principle, this can be done via two different mechanisms in which DMN-CoA is either converted into the corresponding carnitine ester or hydrolyzed to 4,8-dimethylnonanoic acid plus CoASH.(PMID: 11785945 ). Phytanic acid (3,7,11,15-tetramethylhexadecanoic acid) and pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) are branched-chain fatty acids that are constituents of the human diet. As phytanic acid possesses a beta-methyl group, it cannot be degraded by beta-oxidation. Instead, phytanic acid is first degraded by alpha-oxidation, yielding pristanic acid, which is subsequently degraded by beta-oxidation. Phytanic acid alpha-oxidation is thought to occur partly, and pristanic acid beta-oxidation exclusively, in peroxisomes. Accumulation of phytanic acid and pristanic acid is found in blood and tissues of patients affected with generalized peroxisomal disorders.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,8-Dimethylnonanoylcarnitine	ChEBI

Chemical Formula

C₁₈H₃₅NO₄

Average Molecular Weight

329.4748

Monoisotopic Molecular Weight

329.256608613

IUPAC Name

3-[(4,8-dimethylnonanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

4,8-dimethylnonanoylcarnitine

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C18H35NO4/c1-14(2)8-7-9-15(3)10-11-18(22)23-16(12-17(20)21)13-19(4,5)6/h14-16H,7-13H2,1-6H3

InChI Key

DDTDJDZHDFMZED-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
Branched fatty acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:63874 )
O-acylcarnitine (CHEBI:63874 )
ammonium betaine (CHEBI:63874 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006202)
Peroxisome (HMDB: HMDB0006202)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006202)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006202)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006202)

Source

Endogenous

Endogenous (HMDB: HMDB0006202)

Animal

Animal (HMDB: HMDB0006202)

Exogenous

Food

Food (HMDB: HMDB0006202)

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)

Exogenous (HMDB: HMDB0006202)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006202)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006202)
Oxidation of Branched-Chain Fatty Acids (PathBank: SMP0087255)

Lipid metabolism pathway (HMDB: HMDB0006202)

Cellular process

Cell signaling (HMDB: HMDB0006202)

Biochemical process

Lipid transport (HMDB: HMDB0006202)

Role

Biological role

Energy source (HMDB: HMDB0006202)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006202)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.5	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.29	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	13	ChemAxon
Refractivity	113.97 m³·mol⁻¹	ChemAxon
Polarizability	38.58 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

HMDB0006202

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023834

KNApSAcK ID

Not Available

Chemspider ID

21233922

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2365396

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477801

PDB ID

Not Available

ChEBI ID

63874

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4,8 Dimethylnonanoyl carnitine (CFc000002657)

MOL for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

3D MOL for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

3D SDF for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

3D-SDF for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

PDB for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

3D PDB for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

SMILES for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

INCHI for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

Structure for CFc000002657 (4,8 Dimethylnonanoyl carnitine)

3D Structure for CFc000002657 (4,8 Dimethylnonanoyl carnitine)