<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4357</id>
  <title>T3D4303</title>
  <common-name>3-Hydroxybutyric acid</common-name>
  <description>3-Hydroxybutyric acid (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In humans, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-Hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life.  (A3393).</description>
  <cas>300-85-6</cas>
  <pubchem-id>441</pubchem-id>
  <chemical-formula>C4H8O3</chemical-formula>
  <weight>104.1</weight>
  <appearance>White powder.</appearance>
  <melting-point>46°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>444 mg/mL</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">2014-08-29T06:17:27Z</created-at>
  <updated-at type="dateTime">2026-05-14T19:58:19Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>3-Hydroxybutyric acid</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C01089</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>20067</chebi-id>
  <biocyc-id>CPD-335</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB16506</drugbank-id>
  <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)CC(O)=O</moldb-smiles>
  <moldb-formula>C4H8O3</moldb-formula>
  <moldb-inchi>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)</moldb-inchi>
  <moldb-inchikey>WHBMMWSBFZVSSR-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">104.1045</moldb-average-mass>
  <moldb-mono-mass type="decimal">104.047344122</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-0.39</logp>
  <hmdb-id>HMDB00357</hmdb-id>
  <chembl-id>CHEMBL1162496</chembl-id>
  <chemspider-id>428</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>Yang, Wenling; Ma, Peisheng; Wang, Jianing; Wang, Chunfang; Li, Haixia.  Study on the process of chemical synthesis of 3-hydroxybutyric acid.    Huaxue Gongcheng (Xi'an, China)  (2002),  30(5),  74-78.</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003263</chemdb-id>
  <dsstox-id>DTXSID60859511</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>3-hydroxybutanoic acid</iupac>
  <moldb-polar-surface-area>57.53</moldb-polar-surface-area>
  <moldb-refractivity>23.4641</moldb-refractivity>
  <moldb-polarizability>10.005337398683004</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>4.406291419798768</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-2.6205133689113183</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-0.50</moldb-alogps-logp>
  <moldb-alogps-logs>0.71</moldb-alogps-logs>
  <moldb-alogps-solubility>5.39e+02 g/l</moldb-alogps-solubility>
</compound>
