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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-08 14:58:43 UTC
Update Date2019-07-23 06:03:28 UTC
HMDB IDHMDB0029171
Secondary Accession Numbers
  • HMDB29171
Metabolite Identification
Common Name3-Hydroxyadipic acid 3,6-lactone
Description3-hydroxyadipic acid 3,6-lactone is an urinary organic acid. It's level in urine is markedly increased during fasting and in some forms of dicarboxylic aciduria. (PMID: 2739576 )
Structure
Data?1563861808
Synonyms
ValueSource
(5-Oxotetrahydrofuran-2-yl)acetic acidHMDB
2-Furanacetic acidHMDB
3-HA-3,6-laMeSH
Chemical FormulaC6H8O4
Average Molecular Weight144.1253
Monoisotopic Molecular Weight144.042258744
IUPAC Name2-(5-oxooxolan-2-yl)acetic acid
Traditional Name(5-oxooxolan-2-yl)acetic acid
CAS Registry Number60551-20-4
SMILES
[H]OC(=O)CC1([H])CCC(=O)O1
InChI Identifier
InChI=1S/C6H8O4/c7-5(8)3-4-1-2-6(9)10-4/h4H,1-3H2,(H,7,8)
InChI KeyBWEICTHJUIJQPH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Role

Biological role:

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 Solubility235 g/LALOGPS
logP0.11ALOGPS
logP-0.076ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.76 m³·mol⁻¹ChemAxon
Polarizability13.14 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9200000000-fc900a34eeb605905df9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-9500000000-bafa60ccc592602dfe8dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-3900000000-588a741042f02175d2dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mt-9600000000-19caed7ae5ce662aba99JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-3e8894774fa2437a1ceaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-5900000000-90d8d1023e15467f7639JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9500000000-080cf78e3e084c5114bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ae72097e461eeccffbabJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID168429
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound194109
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tserng KY, Jin SJ, Hoppel CL, Kerr DS, Genuth SM: Urinary 3-hydroxyadipic acid 3,6-lactone: structural identification and effect of fasting in adults and children. Metabolism. 1989 Jul;38(7):655-61. [PubMed:2739576 ]