| Common Name |
3D,7D,11D-Phytanic acid
| Description |
3D,7D,11D-Phytanic acid is an isomer of Phytanic acid, an unusual 20-carbon branched-chain fatty acid; Phytanic acid accumliates 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 accumliates 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 Molecliar Bases of Inherited Disease).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
((3R,7R,11R)-)3,7,11,15-TetramethylhexadecanoateHMDB
((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acidHMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoateHMDB
3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acidHMDB
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoateHMDB
3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acidHMDB
3D,7D,11D-PhytanateHMDB
D,D,D-PhytanateHMDB
D,D,D-Phytanic acidHMDB
| Chemical Formlia |
C20H40O2
| Average Molecliar Weight |
312.5304
| Monoisotopic Molecliar 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 |
This compound belongs to the class of chemical entities known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Prenol lipids
| Direct Parent |
Acyclic diterpenoids
| Alternative Parents |
Long-chain fatty acids
Methyl-branched fatty acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility8.17e-05 mg/mLALOGPS
logP7.28ALOGPS
logP7.4ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)5.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity95.28 m3·mol-1ChemAxon
Polarizability40.96 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB 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
| NuGOwiki Link |
HMDB00417
| Metagene Link |
HMDB00417
| METLIN ID |
5406
| PubChem Compound |
10380830
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Dihydrotanshinone I
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. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
PMID: 21904526