ChemFOnt: Showing chemical card for Pristanic acid (CFc000000635)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:04 UTC

Chemfont ID

CFc000000635

Molecule Identification

Common Name

Pristanic acid

Definition

Pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) is a terpenoid acid present at micromolar concentrations in the plasma of healthy individuals. It is also found in the lipids from many sources such as freshwater sponges, krill, earthworms, whales, human milk fat, bovine depot fat, butterfat or Californian petroleum. It is usually present in combination with phytanic acid. In humans, pristanic acid is obtained from two sources: either directly from the diet or as the alpha oxidation product of phytanic acid. At physiological concentrations pristanic acid is a natural ligand for PPARalpha. In liver, pristanic acid is degraded by peroxisomal beta oxidation to propionyl-CoA. Together with phytanic acid, pristanic acid accumulates in several inherited disorders such as Zellweger syndrome. Pristanic acid is a branched chain fatty acid that arises from the breakdown of phytanic acid. It is present at micromolar concentrations in the plasma of healthy individuals. Pristanic acid is normally degraded by peroxisomal beta-oxidation. In patients affected with generalized peroxisomal disorders, degradation of both phytanic acid and pristanic acid is impaired owing to absence of functional peroxisomes. Pristanic acid has been found to activate the peroxisome proliferator-activated receptor {alpha} (PPAR{alpha}) in a concentration dependent manner.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6,10,14-Tetramethyl-pentadecansaeure	ChEBI
2,6,10,14-Tetramethylpentadecylic acid	ChEBI
Acide pristanique	ChEBI
Acido pristanico	ChEBI
Pristaninsaeure	ChEBI
2,6,10,14-Tetramethylpentadecylate	Generator
Pristanate	Generator
(2S)-Pristanic acid	HMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoate	HMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoic acid	HMDB
(2S,6R,10R)-Pristanic acid	HMDB
2,6,10,14-Tetramethylpentadecanoate	HMDB
2,6,10,14-Tetramethylpentadecanoic acid	HMDB
Pristanate:(2S,6R,10R)-pristanate	HMDB

Chemical Formula

C₁₉H₃₈O₂

Average Molecular Weight

298.511

Monoisotopic Molecular Weight

298.287180464

IUPAC Name

2,6,10,14-tetramethylpentadecanoic acid

Traditional Name

pristanic acid

CAS Registry Number

1189-37-3

SMILES

CC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O

InChI Identifier

InChI=1S/C19H38O2/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19(20)21/h15-18H,6-14H2,1-5H3,(H,20,21)

InChI Key

PAHGJZDQXIOYTH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:51340 )
branched-chain saturated fatty acid (CHEBI:51340 )
methyl-branched fatty acid (CHEBI:51340 )
Acyclic diterpenoids (LMPR0104010022 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Adrenoleukodystrophy (HMDB: HMDB0000795)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9818927)

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0000795)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000795)

Fibroblasts (HMDB: HMDB0000795)
Neuron (HMDB: HMDB0000795)

Organ

Prostate (HMDB: HMDB0000795)

Excreta

Biofluid or Excreta

Feces (PMID: 29808030)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000795)

Source

Endogenous

Endogenous (HMDB: HMDB0000795)

Animal

Animal (HMDB: HMDB0000795)

Exogenous

Food

Food (HMDB: HMDB0000795)

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)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0000795)

Process

Role

Biological role

Energy source (HMDB: HMDB0000795)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000795)

Pharmaceutical industry

Biomarker

Zellweger Syndrome (MarkerDB: MDB00000255)
Alpha Methylacyl Co A Racemase Deficiency (MarkerDB: MDB00000255)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	6.9	ALOGPS
logP	7.22	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	90.7 m³·mol⁻¹	ChemAxon
Polarizability	38.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000795

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012993

KNApSAcK ID

Not Available

Chemspider ID

110458

KEGG Compound ID

Not Available

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

51340

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Nakajima, Kenji; Sato, Akio. Microbial oxidation of isoprenoid hydrocarbons. Part II. Production of pristanol and pristanic acid from pristane by Nocardia sp. BPM 1613. Nippon Nogei Kagaku Kaishi (1981), 55(9), 825-8.

Showing chemical card for Pristanic acid (CFc000000635)

MOL for CFc000000635 (Pristanic acid)

3D MOL for CFc000000635 (Pristanic acid)

3D SDF for CFc000000635 (Pristanic acid)

3D-SDF for CFc000000635 (Pristanic acid)

PDB for CFc000000635 (Pristanic acid)

3D PDB for CFc000000635 (Pristanic acid)

SMILES for CFc000000635 (Pristanic acid)

INCHI for CFc000000635 (Pristanic acid)

Structure for CFc000000635 (Pristanic acid)

3D Structure for CFc000000635 (Pristanic acid)