ChemFOnt: Showing chemical card for 3D,7D,11D-Phytanic acid (CFc000000316)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:40 UTC

Chemfont ID

CFc000000316

Molecule Identification

Common Name

3D,7D,11D-Phytanic acid

Definition

3D,7D,11D-Phytanic acid is an isomer of Phytanic acid, an unusual 20-carbon branched-chain fatty acid; Phytanic acid accumulates in blood and tissues of patients with Refsum disease (RD, an inborn error of lipid metabolism inherited as an autosomal recessive trait (OMIM 266500 )), and is a reliable identifier of RD from a large number of other neurological disorders. Phytanic acid also accumulates in a number of other disorders with a very different clinical course: disorders of peroxisome biogenesis (Zellweger syndrome (OMIM 214100 ), neonatal adrenoleukodystrophy (OMIM 202370 ), infantile Refsum disease (OMIM 266510 )) and rhizomelic chondrodysplasia punctata, type 1 (OMIM 215100 ). Phytanic acid is a 3-methyl fatty acid that cannot be beta-oxidized directly, and first undergoes an alpha-oxidation a reaction catalyzed by the enzyme phytanoyl-CoA hydroxylase, which is deficient in RD, the only true disorder of phytanic acid alpha-oxidation. (The Metabolic and Molecular Bases of Inherited Disease).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3D,7D,11D-Phytanate	Generator
((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoate	HMDB
((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acid	HMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoate	HMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acid	HMDB
3,7,11,15-Tetramethyl-[3R-(3R,7R,11R*)]-hexadecanoate	HMDB
3,7,11,15-Tetramethyl-[3R-(3R,7R,11R*)]-hexadecanoic acid	HMDB
D,D,D-Phytanate	HMDB
D,D,D-Phytanic acid	HMDB
(3R,7R,11R)-1-Phytanoate	HMDB

Chemical Formula

C₂₀H₄₀O₂

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

IUPAC Name

(3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid

Traditional Name

phytanoic acid

CAS Registry Number

18654-64-3

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](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)/t17-,18-,19-/m1/s1

InChI Key

RLCKHJSFHOZMDR-GUDVDZBRSA-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

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000417)

Source

Endogenous

Endogenous (HMDB: HMDB0000417)

Animal

Animal (HMDB: HMDB0000417)

Exogenous

Food

Food (HMDB: HMDB0000417)

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

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0000417)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000417)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000417)

Lipid metabolism pathway (HMDB: HMDB0000417)

Cellular process

Cell signaling (HMDB: HMDB0000417)

Biochemical process

Lipid transport (HMDB: HMDB0000417)

Role

Biological role

Energy source (HMDB: HMDB0000417)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000417)

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	40.96 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

HMDB0000417

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013514

KNApSAcK ID

Not Available

Chemspider ID

8556273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5406

PubChem Compound

10380830

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Sita, Lawrence R. Convenient highly stereoselective syntheses of (3R,7R,11R)- and (3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid (phytanic acid) and the corresponding 3,7,11,15-tetramethylhexadecan-1-ols. Journal of Organic Chemistry (1993), 58(19), 5285-7.

Showing chemical card for 3D,7D,11D-Phytanic acid (CFc000000316)

MOL for CFc000000316 (3D,7D,11D-Phytanic acid)

3D MOL for CFc000000316 (3D,7D,11D-Phytanic acid)

3D SDF for CFc000000316 (3D,7D,11D-Phytanic acid)

3D-SDF for CFc000000316 (3D,7D,11D-Phytanic acid)

PDB for CFc000000316 (3D,7D,11D-Phytanic acid)

3D PDB for CFc000000316 (3D,7D,11D-Phytanic acid)

SMILES for CFc000000316 (3D,7D,11D-Phytanic acid)

INCHI for CFc000000316 (3D,7D,11D-Phytanic acid)

Structure for CFc000000316 (3D,7D,11D-Phytanic acid)

3D Structure for CFc000000316 (3D,7D,11D-Phytanic acid)