CHEBI:30887 - isocitric acid

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ChEBI Name isocitric acid ChEBI ID CHEBI:30887 Definition A tricarboxylic acid that is propan-1-ol with a hydrogen at each of the 3 carbon positions replaced by a carboxy group. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:5998, CHEBI:24886 Supplier Information No supplier information found for this compound. Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Isocitric acid is a structural isomer of citric acid. Since citric acid and isocitric acid are structural isomers, they share similar physical and chemical properties. Due to these similar properties, it is difficult to separate the isomers. Salts and esters of isocitric acid are known as isocitrates. The isocitrate anion is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase. Isocitric acid is commonly used as a marker to detect the authenticity and quality of fruit products, most often citrus juices. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. An isocitric acid value higher than this may be indicative of fruit juice adulteration. Isocitric acid has largely been used as a biochemical agent due to limited amounts. However, isocitric acid has been shown to have pharmaceutical and therapeutic effects. Isocitric acid has been shown to effectively treat iron deficient anemia. Additionally, isocitric acid could be used to treat Parkinson's disease. Yarrowia lipolytica can be used to produce isocitric acid and is inexpensive compared to other methods. Furthermore, other methods produce unequal amounts of citric acid to isocitric acid ratio, mostly producing citric acid. Use of Yarrowia lipolytica produces a better yield, making equal amounts of citric acid to isocitric acid. Read full article at Wikipedia Formula C6H8O7 Net Charge 0 Average Mass 192.12352 Monoisotopic Mass 192.02700 InChI InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13) InChIKey ODBLHEXUDAPZAU-UHFFFAOYSA-N SMILES OC(C(CC(O)=O)C(O)=O)C(O)=O Metabolite of Species Details Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed Roles Classification Chemical Role(s): Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Biological Role(s): fundamental metabolite Any metabolite produced by all living cells. View more via ChEBI Ontology ChEBI Ontology Outgoing isocitric acid (CHEBI:30887) has role fundamental metabolite (CHEBI:78675) isocitric acid (CHEBI:30887) is a secondary alcohol (CHEBI:35681) isocitric acid (CHEBI:30887) is a tricarboxylic acid (CHEBI:27093) isocitric acid (CHEBI:30887) is conjugate acid of isocitrate(1−) (CHEBI:36454) Incoming 2-caffeoylisocitric acid (CHEBI:16166) has functional parent isocitric acid (CHEBI:30887) methylisocitric acid (CHEBI:25311) has functional parent isocitric acid (CHEBI:30887) D-erythro-isocitric acid (CHEBI:160) is a isocitric acid (CHEBI:30887) D-threo-isocitric acid (CHEBI:151) is a isocitric acid (CHEBI:30887) L-erythro-isocitric acid (CHEBI:43291) is a isocitric acid (CHEBI:30887) L-threo-isocitric acid (CHEBI:30889) is a isocitric acid (CHEBI:30887) isocitrate(1−) (CHEBI:36454) is conjugate base of isocitric acid (CHEBI:30887) IUPAC Names 1-hydroxypropane-1,2,3-tricarboxylic acid 3-carboxy-2,3-dideoxypentaric acid Synonyms Sources 1-Hydroxypropane-1,2,3-tricarboxylic acid KEGG COMPOUND 1-Hydroxytricarballylic acid KEGG COMPOUND Isocitric acid KEGG COMPOUND Manual Xrefs Databases C00001188 KNApSAcK C00311 KEGG COMPOUND DB01727 DrugBank ECMDB04088 ECMDB HMDB0000193 HMDB Isocitrate MetaCyc Isocitric_acid Wikipedia YMDB00026 YMDB View more database links Registry Numbers Types Sources 1727945 Reaxys Registry Number Reaxys 320-77-4 CAS Registry Number KEGG COMPOUND 320-77-4 CAS Registry Number ChemIDplus Citations Types Sources 17439666 PubMed citation Europe PMC 23989918 PubMed citation Europe PMC 24702026 PubMed citation Europe PMC Last Modified 08 November 2018