<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4482</id>
  <title>T3D4428</title>
  <common-name>2-Methylcitric acid</common-name>
  <description>2-Methylcitric acid is an endogenous organic compound with the formula C7H10O7 and an average molecular weight of 206.15 g/mol. It exists as a solid at room temperature. 2-Methylcitric acid belongs to the tricarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds.

The compound is found in or released from six recorded sources. These include household cleaning and consumer products, specifically soap detergents, perfumes within detergents and soaps, and tobacco smoke filters. It is also associated with electrical and electronic equipment, such as hybrid capacitors and electrodes, as well as food preservation within food, food processing and cookware.

In a clinical context, 2-methylcitric acid is elevated in the body fluids of patients with multiple carboxylase deficiency, methylmalonic aciduria, and propionic acidaemia. It is formed by the enzyme si-citrate synthase through the condensation of oxalacetate and accumulated propionyl-CoA. The molecule contains two stereogenic centers, allowing for the existence of four stereoisomers; however, only the (2S, 3S) and (2R, 3S) stereoisomers have been identified in human urine.</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>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic acids and derivatives</superklass>
  <klass>Carboxylic acids and derivatives</klass>
  <subklass>Tricarboxylic acids and derivatives</subklass>
  <paper-count type="integer">378</paper-count>
  <sync-id>CED0012259</sync-id>
  <structure-inchikey>YNOXCRMFGMSKIJ-UHFFFAOYSA-N</structure-inchikey>
  <structure-fingerprint>400000000000000000008000000020000000000000000000000000000000000000000010000000000000000000000000040000000000000000000000000000000000000000000000000000000000000000200000000000000000000400000000000000000100000000000000000200000000000000800000000000000000000000000000c4000000000000000000000000000000000000000000000000000000000000000000000000080000000000000000000000000000000000000000000000000000000000000000000000008000000000000000000000400000000000000000000000020800000008000000080400000000000000400000000000000000</structure-fingerprint>
  <structure-pattern-fingerprint>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</structure-pattern-fingerprint>
  <structure-pickle>ï¾­Þ�����������������������€���`�������`�������(�������h��������(������� ������`�������`�������(�������h��������(�������(�������h��������(�������������� ��(��������������	 �
(������ �(�B��������������</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:01:16Z</structure-indexed-at>
</compound>
