<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4309</id>
  <title>T3D4255</title>
  <common-name>2-Methyl-3-hydroxybutyric acid</common-name>
  <description>3-Hydroxy-2-methyl-butanoic acid (HMBA) is a normal urinary metabolite involved in the isoleucine catabolism, as well as presumably beta-oxidation of fatty acids and ketogenesis, excreted in abnormally high amounts in beta-ketothiolase deficiency. Differences in the enantiomeric ratio of HMBA may originate from the enantioselectivity of different enzyme systems  (A3337).</description>
  <cas>473-86-9</cas>
  <pubchem-id>160471</pubchem-id>
  <chemical-formula>C5H10O3</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">2014-08-29T06:07:40Z</created-at>
  <updated-at type="dateTime">2026-04-02T23:44:51Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id>37051</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(O)C(C)C(O)=O</moldb-smiles>
  <moldb-formula>C5H10O3</moldb-formula>
  <moldb-inchi>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)</moldb-inchi>
  <moldb-inchikey>VEXDRERIMPLZLU-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">118.1311</moldb-average-mass>
  <moldb-mono-mass type="decimal">118.062994186</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB00354</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>141015</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>Inoue, Yoshio; Sano, Fumitaka; Nakamura, Kazuhiro; Yoshie, Naoko; Saito, Yuji; Satoh, Hiroyasu; Mino, Takashi; Matsuo, Tomonori; Doi, Yoshiharu.  Microstructure of copoly(3-hydroxyalkanoates) produced in the anaerobic-aerobic activated sludge process.  Polymer International  (1996),  39(3),  183-9.</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003215</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00014715</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>57.53</moldb-polar-surface-area>
  <moldb-refractivity>28.038600000000002</moldb-refractivity>
  <moldb-polarizability>11.829094147373619</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>4.513689206767185</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.7866129389831196</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-0.13</moldb-alogps-logp>
  <moldb-alogps-logs>0.45</moldb-alogps-logs>
  <moldb-alogps-solubility>3.36e+02 g/l</moldb-alogps-solubility>
</compound>
