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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-08 14:58:43 UTC
Update Date2023-02-21 17:18:39 UTC
HMDB IDHMDB0029171
Secondary Accession Numbers
  • HMDB29171
Metabolite Identification
Common Name3-Hydroxyadipic acid 3,6-lactone
Description3-Hydroxyadipic acid 3,6-lactone, also known as (5-oxotetrahydrofuran-2-yl)acetic acid or 2-furanacetic acid, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones 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. 3-Hydroxyadipic acid 3,6-lactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyadipic acid 3,6-lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxyadipic acid 3,6-lactone.
Structure
Data?1676999919
Synonyms
ValueSource
3-Hydroxyadipate 3,6-lactoneGenerator
(5-Oxotetrahydrofuran-2-yl)acetic acidHMDB
2-Furanacetic acidHMDB
3-HA-3,6-laHMDB
2-(5-Oxooxolan-2-yl)acetateHMDB
3-Hydroxyadipic acid 3,6-lactoneMeSH
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
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.36731661259
DarkChem[M-H]-125.30231661259
DeepCCS[M+H]+131.61630932474
DeepCCS[M-H]-129.07130932474
DeepCCS[M-2H]-165.130932474
DeepCCS[M+Na]+140.05530932474
AllCCS[M+H]+131.632859911
AllCCS[M+H-H2O]+127.232859911
AllCCS[M+NH4]+135.732859911
AllCCS[M+Na]+136.932859911
AllCCS[M-H]-127.532859911
AllCCS[M+Na-2H]-129.232859911
AllCCS[M+HCOO]-131.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxyadipic acid 3,6-lactone[H]OC(=O)CC1([H])CCC(=O)O12179.8Standard polar33892256
3-Hydroxyadipic acid 3,6-lactone[H]OC(=O)CC1([H])CCC(=O)O11179.3Standard non polar33892256
3-Hydroxyadipic acid 3,6-lactone[H]OC(=O)CC1([H])CCC(=O)O11335.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyadipic acid 3,6-lactone,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1CCC(=O)O11433.0Semi standard non polar33892256
3-Hydroxyadipic acid 3,6-lactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1CCC(=O)O11681.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9200000000-fc900a34eeb605905df92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-9500000000-bafa60ccc592602dfe8d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Positive-QTOFsplash10-004j-3900000000-588a741042f02175d2db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Positive-QTOFsplash10-00mt-9600000000-19caed7ae5ce662aba992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Positive-QTOFsplash10-00ku-9000000000-3e8894774fa2437a1cea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Negative-QTOFsplash10-0007-5900000000-90d8d1023e15467f76392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Negative-QTOFsplash10-0002-9500000000-080cf78e3e084c5114bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Negative-QTOFsplash10-0006-9000000000-ae72097e461eeccffbab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Positive-QTOFsplash10-0002-9300000000-e2e26bc548ea5e45deb42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Positive-QTOFsplash10-053m-9000000000-bdb61c552e244b22efc22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Positive-QTOFsplash10-052f-9000000000-b633d0c80af91209ccd12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 10V, Negative-QTOFsplash10-0005-9400000000-c8d72a43df3e70e601b82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 20V, Negative-QTOFsplash10-006t-9000000000-a9ae910b51717834c1b92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyadipic acid 3,6-lactone 40V, Negative-QTOFsplash10-052f-9000000000-0c20aafa91b0aa7ba3a92021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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
FooDB IDFDB111656
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 ID173603
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 ]