1.0 2010-04-08 22:06:08 UTC 2025-11-18 22:55:30 UTC FDB004207 beta-Hydroxy-beta-methylglutaric acid 3-hydroxymethylglutaric acid, also known as meglutol or dicrotalic acid, is a member of the class of compounds known as hydroxy fatty acids. Hydroxy fatty acids are fatty acids in which the chain bears a hydroxyl group. 3-hydroxymethylglutaric acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3-hydroxymethylglutaric acid can be synthesized from glutaric acid. 3-hydroxymethylglutaric acid is also a parent compound for other transformation products, including but not limited to, viscumneoside VII, viscumneoside IV, and yanuthone D. 3-hydroxymethylglutaric acid can be found in flaxseed, which makes 3-hydroxymethylglutaric acid a potential biomarker for the consumption of this food product. 3-hydroxymethylglutaric acid can be found primarily in saliva and urine. 3-hydroxymethylglutaric acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronically high levels of 3-hydroxymethylglutaric acid are associated with the inborn error of metabolism: 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency (T3DB). C6H10O5 162.1406 162.05282343 3-hydroxy-3-methylpentanedioic acid meglutol CC(O)(CC(O)=O)CC(O)=O InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10) NPOAOTPXWNWTSH-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Hydroxy fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Methyl-branched fatty acids Organic oxides Short-chain hydroxy acids and derivatives Tertiary alcohols Alcohol Aliphatic acyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Hydroxy fatty acid Methyl-branched fatty acid Organic oxide Organic oxygen compound Organooxygen compound Short-chain hydroxy acid Tertiary alcohol 3-hydroxy carboxylic acid dicarboxylic acid tertiary alcohol logp -0.88 ALOGPS logs 0.23 ALOGPS solubility 2.75e+02 g/l ALOGPS logp -0.75 ChemAxon pka_strongest_acidic 3.68 ChemAxon pka_strongest_basic -3 ChemAxon iupac 3-hydroxy-3-methylpentanedioic acid ChemAxon average_mass 162.1406 ChemAxon mono_mass 162.05282343 ChemAxon smiles CC(O)(CC(O)=O)CC(O)=O ChemAxon formula C6H10O5 ChemAxon inchi InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10) ChemAxon inchikey NPOAOTPXWNWTSH-UHFFFAOYSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 34.14 ChemAxon polarizability 14.55 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 445 Specdb::MsIr 446 Specdb::MsIr 447 Specdb::NmrTwoD 1284 Specdb::NmrOneD 1342 Specdb::CMs 542 Specdb::CMs 1288 Specdb::CMs 26625 Specdb::CMs 30141 Specdb::CMs 30439 Specdb::CMs 31130 Specdb::CMs 32048 Specdb::CMs 37459 Specdb::CMs 135436 Specdb::CMs 143170 Specdb::CMs 1059356 Specdb::CMs 1059357 Specdb::CMs 1059359 Specdb::CMs 1059360 Specdb::CMs 1059362 Specdb::CMs 1059364 Specdb::CMs 1059366 Specdb::CMs 1059368 Specdb::CMs 1059369 Specdb::MsMs 567 Specdb::MsMs 568 Specdb::MsMs 569 Specdb::MsMs 4023 Specdb::MsMs 4024 Specdb::MsMs 4025 Specdb::MsMs 4026 Specdb::MsMs 4027 Specdb::MsMs 4029 Specdb::MsMs 4030 Specdb::MsMs 7994 Specdb::MsMs 7995 Specdb::MsMs 7996 Specdb::MsMs 14666 Specdb::MsMs 14667 Specdb::MsMs 14668 Specdb::MsMs 437895 Specdb::MsMs 437896 Specdb::MsMs 437897 Specdb::MsMs 437898 Specdb::MsMs 437899 Specdb::MsMs 439222 Specdb::MsMs 448165 Specdb::MsMs 2233825 Specdb::MsMs 2235141 HMDB0000355 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 Flaxseed Type 1 specific Linum usitatissimum 4006 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 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Oat Type 1 specific Avena sativa 4498 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