ChemFOnt: Showing chemical card for Phytanic acid (CFc000000639)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:05 UTC

Chemfont ID

CFc000000639

Molecule Identification

Common Name

Phytanic acid

Definition

Phytanic acid (or 3,7,11,15-tetramethylhexadecanoic acid) is a 20-carbon branched-chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish. It is primarily formed by bacterial degradation of chlorophyll in the intestinal tract of ruminants. Unlike most fatty acids, phytanic acid cannot be metabolized by beta-oxidation (because of a methyl group in the beta position). Instead, it undergoes alpha-oxidation in the peroxisome, where it is converted into pristanic acid by the removal of one carbon. Pristanic acid can undergo several rounds of beta-oxidation in the peroxisome to form medium-chain fatty acids that can be converted into carbon dioxide and water in mitochondria. Refsum disease, an autosomal recessive neurological disorder caused by mutations in the PHYH gene, is characterized by having impaired alpha-oxidation activity. Individuals with Refsum disease accumulate large stores of phytanic acid in their blood and tissues. This frequently leads to peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss. Therefore, chronically high levels of phytanic acid can be neurotoxic. Phytanic acid's neurotoxicity appears to lie in its ability to initiate astrocyte/neural cell death by activating the mitochondrial route of apoptosis. In particular, phytanic acid can induce the substantial generation of reactive oxygen species in isolated mitochondria as well as in intact cells. It also induces the release of cytochrome c from mitochondria.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,7,11,15-Tetramethyl hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecansaeure	ChEBI
3,7,11,15-Tetramethylhexadecanoic acid	Kegg
3,7,11,15-Tetramethyl hexadecanoate	Generator
3,7,11,15-Tetramethyl-hexadecanoate	Generator
3,7,11,15-Tetramethylhexadecanoate	Generator
Phytanate	Generator
3,7,11,15-Tetramethylhexadecoanoate	HMDB
3,7,11,15-Tetramethylhexadecoanoic acid	HMDB
Phytanoate	HMDB
Phytanoic acid	HMDB
Acid, phytanic	HMDB

Chemical Formula

C₂₀H₄₀O₂

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

IUPAC Name

3,7,11,15-tetramethylhexadecanoic acid

Traditional Name

phytanic acid

CAS Registry Number

14721-66-5

SMILES

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

InChI Identifier

InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)

InChI Key

RLCKHJSFHOZMDR-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:16285 )
branched-chain saturated fatty acid (CHEBI:16285 )
methyl-branched fatty acid (CHEBI:16285 )
Acyclic diterpenoids (C01607 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Adrenoleukodystrophy (HMDB: HMDB0000801)
Refsum's disease (HMDB: HMDB0000801)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12700346)

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0000801)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000801)

Fibroblasts (HMDB: HMDB0000801)
Neuron (HMDB: HMDB0000801)

Organ

Liver (HMDB: HMDB0000801)
Prostate (HMDB: HMDB0000801)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000801)

Source

Endogenous

Endogenous (HMDB: HMDB0000801)

Animal

Animal (HMDB: HMDB0000801)

Exogenous

Food

Food (HMDB: HMDB0000801)
Red meat (HMDB: HMDB0000801)

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)

Milk and milk product

Dairy products (HMDB: HMDB0000801)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0000801)

Process

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.2e-05 g/L	ALOGPS
logP	7.28	ALOGPS
logP	7.4	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	5.04	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	14	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	41.09 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

HMDB0000801

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022252

KNApSAcK ID

Not Available

Chemspider ID

25001

KEGG Compound ID

C01607

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16285

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Karrer, P.; Epprecht, A.; Konig, Hans. General method of preparation for 2-methyl-3-alkylnaphthoquinones. Constitution and vitamin K activity. Helvetica Chimica Acta (1940), 23 272-83.

Showing chemical card for Phytanic acid (CFc000000639)

MOL for CFc000000639 (Phytanic acid)

3D MOL for CFc000000639 (Phytanic acid)

3D SDF for CFc000000639 (Phytanic acid)

3D-SDF for CFc000000639 (Phytanic acid)

PDB for CFc000000639 (Phytanic acid)

3D PDB for CFc000000639 (Phytanic acid)

SMILES for CFc000000639 (Phytanic acid)

INCHI for CFc000000639 (Phytanic acid)

Structure for CFc000000639 (Phytanic acid)

3D Structure for CFc000000639 (Phytanic acid)