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Record Information
Version3.6
Creation Date2006-05-22 14:17:41 UTC
Update Date2016-02-11 01:05:26 UTC
HMDB IDHMDB02203
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxycapric acid
Description3-hydroxycapric acid is a normally occurring carboxylic acid in human blood plasma. Medium- and long-chain 3-hydroxymonocarboxylic acids represent intermediates in the beta-oxidation of fatty acids. They accumulate in the plasma of patients with an inherited deficiency of long-chain 3-hydroxyacylCoA dehydrogenase [EC 1.1.1.35]. (PMID: 1912723 ). 3-hydroxyacyl-CoA dehydrogenase deficiency (HADH) has been described in diverse clinical cases: in cases of juvenile-onset recurrent myoglobinuria, hypoketotic hypoglycemic encephalopathy, in hypertrophic/dilatative cardiomyopathy, in sudden infant death, and in fulminant hepatic failure. (OMIM 231530 ). 3-hydroxycapric acid has some shape-transforming action on the membrane of intact human erythrocytes. (PMID: 7318031 ).
Structure
Thumb
Synonyms
ValueSource
(+/-)3-hydroxy-decanoateHMDB
(+/-)3-hydroxy-decanoic acidHMDB
10:0(3-OH)HMDB
3-HDAHMDB
3-Hydroxy-decanoateHMDB
3-Hydroxy-decanoic acidHMDB
3-HydroxydecanoateHMDB
beta-HydroxydecanoateHMDB
beta-Hydroxydecanoic acidHMDB
MyrmicacinHMDB
Chemical FormulaC10H20O3
Average Molecular Weight188.264
Monoisotopic Molecular Weight188.141244506
IUPAC Name3-hydroxydecanoic acid
Traditional Nameβ-hydroxydecanoic acid
CAS Registry Number14292-26-3
SMILES
CCCCCCCC(O)CC(O)=O
InChI Identifier
InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)
InChI KeyInChIKey=FYSSBMZUBSBFJL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.74 mg/mLALOGPS
logP2.6ALOGPS
logP2.36ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity50.99 m3·mol-1ChemAxon
Polarizability22.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0f89-3950000000-4dc7506e884d7c6679d5View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022904
KNApSAcK IDNot Available
Chemspider ID24790
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02203
Metagene LinkHMDB02203
METLIN ID6544
PubChem Compound26612
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceKondo, Kiyoshi; Ryu, Yuchin. 3-Hydroxydecanoic acid. Jpn. Kokai Tokkyo Koho (1972), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [7320161 ]
  2. Dorland L, Ketting D, Bruinvis L, Duran M: Medium- and long-chain 3-hydroxymonocarboxylic acids: analysis by gas chromatography combined with mass spectrometry. Biomed Chromatogr. 1991 Jul;5(4):161-4. [1912723 ]
  3. Kanaho Y, Sato T, Fujii T, Iwanami Y, Iwadare T, Orito K: Shape-transforming action of myrmicacin (3-hydroxydecanoic acid) and some related compounds on the membrane of intact human erythrocytes. Chem Pharm Bull (Tokyo). 1981 Oct;29(10):3063-6. [7318031 ]