1.0 2020-04-17 19:13:03 UTC 2020-12-07 19:11:39 UTC CDB005137 2-Hydroxyglutarate 2-Hydroxyglutarate belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. 2-Hydroxyglutarate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxyglutarate exists in all living species, ranging from bacteria to humans. 2-hydroxyglutarate can be biosynthesized from oxoglutaric acid through the action of the enzyme L-2-hydroxyglutarate dehydrogenase, mitochondrial. In humans, 2-hydroxyglutarate is involved in the metabolic disorder called the oncogenic action of d-2-hydroxyglutarate in hydroxyglutaric aciduria. In cancer it is either produced by overexpression of phosphoglycerate dehydrogenase (PHGDH) or is produced in excess by gain-of-function mutations in the cytosolic and mitochondrial isoforms of isocitrate dehydrogenase (IDH). A deficiency in either of these two enzymes can lead to a disease known as 2-hydroxyglutaric aciduria. 2-Hydroxyglutarate exists in 2 isomers: L-2-hydroxyglutarate acid and D-2-hydroxyglutarate. D-2-hydroxyglutaric aciduria (caused by loss of D2HGDH or gain of function of IDH) is rare, with symptoms including cancer, macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. 2-Hydroxyglutarate is a potentially toxic compound. 2-Hydroxyglutarate, with regard to humans, has been found to be associated with several diseases such as deafness, onychodystrophy, osteodystrophy, mental retardation, and seizures syndrome, d, l-2-hydroxyglutaric aciduria, supragingival plaque, and colorectal cancer; 2-hydroxyglutarate has also been linked to the inborn metabolic disorder l-2-hydroxyglutaric aciduria. 2-Hydroxyglutarate has also been found to be a metabolite in Aspergillus (PMID: 6057807). 2-hydroxyglutarate is also the product of gain-of-function mutations in the cytosolic and mitochondrial isoforms of isocitrate dehydrogenase (IDH). In humans it is part of butanoate metabolic pathway and can be produced by phosphoglycerate dehydrogenase (PHGDH). Humans have to variants of this enzyme: 2-Hydroxyglutarate dehydrogenase (D2HGDH) and L-2-hydroxyglutarate dehydrogenase (L2HGDH). 2-Hydroxyglutarate is expected to be in Cannabis as all living plants are known to produce and metabolize it. alpha-Hydroxyglutaric acid alpha-Hydroxyglutarate a-Hydroxyglutarate a-Hydroxyglutaric acid Α-hydroxyglutarate Α-hydroxyglutaric acid 2-Hydroxyglutaric acid D-2-Hydroxyglutarate alpha-Hydroxyglutarate, (D)-isomer alpha-Hydroxyglutarate, (DL)-isomer alpha-Hydroxyglutarate, (L)-isomer alpha-Hydroxyglutarate, disodium salt (±)-2-hydroxyglutaric acid 2,3-Dideoxypentaric acid 2-Hydroxypentanedioic acid DL-2-Hydroxyglutaric acid 2-Hydroxyglutarate C5H8O5 148.11 148.0372 2-hydroxypentanedioic acid 2-hydroxyglutaric acid 2889-31-8 OC(CCC(O)=O)C(O)=O InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10) HWXBTNAVRSUOJR-UHFFFAOYSA-N belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. Short-chain hydroxy acids and derivatives Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Short-chain hydroxy acids and derivatives Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives Monosaccharides Organic oxides Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Monosaccharide Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Short-chain hydroxy acid 2-hydroxydicarboxylic acid logp -1.04 ALOGPS logs 0.03 ALOGPS logp -0.82 ChemAxon pka_strongest_acidic 3.28 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 2-hydroxypentanedioic acid ChemAxon average_mass 148.11 ChemAxon mono_mass 148.0372 ChemAxon smiles OC(CCC(O)=O)C(O)=O ChemAxon formula C5H8O5 ChemAxon inchi InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10) ChemAxon inchikey HWXBTNAVRSUOJR-UHFFFAOYSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 29.63 ChemAxon polarizability 12.97 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C02630 42 43 17084 2-HYDROXYGLUTARIC_ACID Alpha-Hydroxyglutaric_acid Bleiweis AS, Reeves HC, Ajl SJ: Formation of alpha-hydroxyglutaric acid by Aspergillus glaucus. J Bacteriol. 1967 Nov;94(5):1560-4. 6057807