<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4482</id>
  <title>T3D4428</title>
  <common-name>2-Methylcitric acid</common-name>
  <description>Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270). MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine.  (A3498).</description>
  <cas>6061-96-7</cas>
  <pubchem-id>515</pubchem-id>
  <chemical-formula>C7H10O7</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:51:14Z</created-at>
  <updated-at type="dateTime">2026-04-06T13:58:54Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id>30835</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC(C(O)=O)C(O)(CC(O)=O)C(O)=O</moldb-smiles>
  <moldb-formula>C7H10O7</moldb-formula>
  <moldb-inchi>InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)</moldb-inchi>
  <moldb-inchikey>YNOXCRMFGMSKIJ-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">206.1501</moldb-average-mass>
  <moldb-mono-mass type="decimal">206.042652674</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB00379</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>500</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander.  Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain.    PCT Int. Appl.  (2007),     30pp.  CODEN: PIXXD2  WO  2007101866  A2  20070913  CAN 147:363646  AN 2007:1033111   </synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003388</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00126979</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>132.13</moldb-polar-surface-area>
  <moldb-refractivity>40.19840000000001</moldb-refractivity>
  <moldb-polarizability>17.21399595260961</moldb-polarizability>
  <moldb-rotatable-bond-count>5</moldb-rotatable-bond-count>
  <moldb-acceptor-count>7</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>3.18324322639043</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-4.260390633991254</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-3</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-0.89</moldb-alogps-logp>
  <moldb-alogps-logs>-0.07</moldb-alogps-logs>
  <moldb-alogps-solubility>1.75e+02 g/l</moldb-alogps-solubility>
</compound>
