1.0 2010-04-08 22:10:45 UTC 2019-11-26 03:08:31 UTC FDB013514 (3R,7R,11R)-1-Phytanoic acid Constituent of butter 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). (3R,7R,11R)-1-Phytanoic acid is found in milk and milk products. ((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoate ((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acid 3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoate 3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acid 3,7,11,15-Tetramethyl-D,D,D-hexadecanoate 3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acid 3D,7D,11D-Phytanate 3D,7D,11D-Phytanic acid D,D,D-Phytanate D,D,D-Phytanic acid Phytanic acid C20H40O2 312.5304 312.302830524 (3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid phytanoic acid 18654-64-3 CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O 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 RLCKHJSFHOZMDR-GUDVDZBRSA-N 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. Acyclic diterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Diterpenoids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Acyclic diterpenoid Aliphatic acyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Hydrocarbon derivative Long-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Solid logp 7.28 ALOGPS logs -6.58 ALOGPS solubility 8.17e-05 g/l ALOGPS logp 7.4 ChemAxon pka_strongest_acidic 5.04 ChemAxon iupac (3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid ChemAxon average_mass 312.5304 ChemAxon mono_mass 312.302830524 ChemAxon smiles CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O ChemAxon formula C20H40O2 ChemAxon inchi 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 ChemAxon inchikey RLCKHJSFHOZMDR-GUDVDZBRSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 95.28 ChemAxon polarizability 40.96 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 70323 Specdb::MsMs 70324 Specdb::MsMs 70325 Specdb::MsMs 128799 Specdb::MsMs 128800 Specdb::MsMs 128801 Specdb::MsMs 2810822 Specdb::MsMs 2810823 Specdb::MsMs 2810824 Specdb::MsMs 2895598 Specdb::MsMs 2895599 Specdb::MsMs 2895600 Specdb::CMs 9525 Specdb::CMs 37517 Specdb::CMs 157171 Specdb::CMs 1061042 HMDB00417 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk and milk products Unknown generic Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823