You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:34 UTC
HMDB IDHMDB00325
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxysuberic acid
Description3-Hydroxysuberic acid is a metabolite derived from the w-oxidation of 3-hydroxy fatty acids and the subsequent beta-oxidation of longer-chain 3-hydroxy dicarboxylic acids (PMID 2001377 ). It has been found increased in ketoaciduria (PMID 1591279 ).
Structure
Thumb
Synonyms
ValueSource
3-HydroxyoctanedioateHMDB
3-Hydroxyoctanedioic acidHMDB
3-HydroxysuberateHMDB
Chemical FormulaC8H14O5
Average Molecular Weight190.1938
Monoisotopic Molecular Weight190.084123558
IUPAC Name3-hydroxyoctanedioic acid
Traditional Name3-hydroxysuberic acid
CAS Registry Number73141-47-6
SMILES
OC(CCCCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C8H14O5/c9-6(5-8(12)13)3-1-2-4-7(10)11/h6,9H,1-5H2,(H,10,11)(H,12,13)
InChI KeyInChIKey=ARJZZFJXSNJKGR-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
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility19.5 mg/mLALOGPS
logP-0.17ALOGPS
logP0.15ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.46 m3·mol-1ChemAxon
Polarizability19.14 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-052r-0900000000-c8110c0a94d4b56b34cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9300000000-4f9255a9b03fdc58054eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00pi-9000000000-cc672b33ccef862ae95bView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.1 (0.1-0.1) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified2.7 (2.7-2.7) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified5.5 (2.0-28.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified2.0 (0.8-5.6) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
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 IDFDB021951
KNApSAcK IDNot Available
Chemspider ID13498677
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00325
Metagene LinkHMDB00325
METLIN ID5314
PubChem Compound22328017
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceChiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J. A convenient general method for the synthesis of hydroxy diacids. Tetrahedron Letters (2007), 48(18), 3141-3143.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  2. Tserng KY, Jin SJ: Metabolic origin of urinary 3-hydroxy dicarboxylic acids. Biochemistry. 1991 Mar 5;30(9):2508-14. [2001377 ]
  3. Verhaeghe BJ, Van Bocxlaer JF, De Leenheer AP: Gas chromatographic/mass spectrometric identification of 3-hydroxydicarboxylic acids in urine. Biol Mass Spectrom. 1992 Jan;21(1):27-32. [1591279 ]