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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:44 UTC
HMDB IDHMDB0000349
Secondary Accession Numbers
  • HMDB0002475
  • HMDB00349
  • HMDB02475
Metabolite Identification
Common NameErythrono-1,4-lactone
DescriptionErythrono-1,4-lactone has been identified as a lactone of tetronic acid in the urine from normal adults and neonates. The formation of this compound may be a consequence of lactonization of erythronic acid during the extraction/isolation process. Lactonization is a potential problem when measuring acids that contain a hydroxyl group at the number 4 carbon, as lactones are formed under acidic conditions. Evidence indicates that most 4-hydroxy acids do not normally exist to any appreciable extent as lactones in urine. (PMID 1192581 ).
Structure
Data?1676999684
Synonyms
ValueSource
D-ErythronolactoneChEBI
Erythronic acid gamma-lactoneChEBI
Erythronate g-lactoneGenerator
Erythronate gamma-lactoneGenerator
Erythronate γ-lactoneGenerator
Erythronic acid g-lactoneGenerator
Erythronic acid γ-lactoneGenerator
(3R,4R)-Dihydro-3,4-dihydroxy-threono-1,4-lactone 2(3H)-furanoneHMDB
(3R,4R)-Rel-dihydro-3,4-dihydroxy-2(3H)-furanoneHMDB
3,4-Dihydroxydihydro-2(3H)-furanoneHMDB
D-Erythronic acid gamma-lactoneHMDB
delta-Erythronic acid gamma-lactoneHMDB
Dihydro-3,4-dihydroxy-cis-2(3H)-furanoneHMDB
Chemical FormulaC4H6O4
Average Molecular Weight118.088
Monoisotopic Molecular Weight118.02660868
IUPAC Name(3R,4R)-3,4-dihydroxyoxolan-2-one
Traditional Nameerythrono-1,4-lactone
CAS Registry Number17675-99-9
SMILES
O[C@@H]1COC(=O)[C@@H]1O
InChI Identifier
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1
InChI KeySGMJBNSHAZVGMC-PWNYCUMCSA-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
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility1240 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS1.02ALOGPS
pKa (Strongest Acidic)11.66ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.85 m³·mol⁻¹ChemAxon
Polarizability9.84 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]+124.08931661259
DarkChem[M-H]-120.05131661259
AllCCS[M+H]+126.52432859911
AllCCS[M-H]-118.24732859911
DeepCCS[M+H]+128.2430932474
DeepCCS[M-H]-126.32630932474
DeepCCS[M-2H]-161.82730932474
DeepCCS[M+Na]+135.96130932474
AllCCS[M+H]+126.532859911
AllCCS[M+H-H2O]+121.732859911
AllCCS[M+NH4]+131.032859911
AllCCS[M+Na]+132.332859911
AllCCS[M-H]-118.232859911
AllCCS[M+Na-2H]-120.832859911
AllCCS[M+HCOO]-123.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Erythrono-1,4-lactoneO[C@@H]1COC(=O)[C@@H]1O2308.9Standard polar33892256
Erythrono-1,4-lactoneO[C@@H]1COC(=O)[C@@H]1O1156.7Standard non polar33892256
Erythrono-1,4-lactoneO[C@@H]1COC(=O)[C@@H]1O1289.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Erythrono-1,4-lactone,1TMS,isomer #1C[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O1296.7Semi standard non polar33892256
Erythrono-1,4-lactone,1TMS,isomer #2C[Si](C)(C)O[C@H]1C(=O)OC[C@H]1O1276.0Semi standard non polar33892256
Erythrono-1,4-lactone,2TMS,isomer #1C[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O[Si](C)(C)C1410.0Semi standard non polar33892256
Erythrono-1,4-lactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O1506.1Semi standard non polar33892256
Erythrono-1,4-lactone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C(=O)OC[C@H]1O1519.2Semi standard non polar33892256
Erythrono-1,4-lactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@@H]1O[Si](C)(C)C(C)(C)C1834.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Erythrono-1,4-lactone GC-MS (2 TMS)splash10-0udi-1920000000-8bf103e6bad44eb52cac2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized)splash10-0udi-1920000000-8bf103e6bad44eb52cac2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-63c53760143cd20448732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (2 TMS) - 70eV, Positivesplash10-0fki-9430000000-f0cfa4e00daeb540aee72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erythrono-1,4-lactone GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Positive-QTOFsplash10-0gb9-1900000000-d7d529471e146551a4702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Positive-QTOFsplash10-0uxr-1900000000-7e70d7eac9b72e1cbd362017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Positive-QTOFsplash10-0a4l-9100000000-7a95b8e64f0d366b41012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Negative-QTOFsplash10-014i-2900000000-c877a9861f0a9e0fa9472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Negative-QTOFsplash10-014j-8900000000-874d13e11592fe389a742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Negative-QTOFsplash10-006x-9000000000-295d5454144b0a74cb002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Negative-QTOFsplash10-00di-9100000000-ccaaa47150cc978a00b92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Negative-QTOFsplash10-0a4l-9000000000-07ca8b081361da8d614e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Negative-QTOFsplash10-0006-9000000000-846eebab9a9caa26cce62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 10V, Positive-QTOFsplash10-0udi-6900000000-fde995765993269b5d052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 20V, Positive-QTOFsplash10-0007-9100000000-11a72527d4f24a67775b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erythrono-1,4-lactone 40V, Positive-QTOFsplash10-0007-9000000000-f1bef05a8557507531322021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C 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 Locations
  • Cytoplasm (predicted from logP)
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 IDFDB021972
KNApSAcK IDC00052984
Chemspider ID4483398
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5338
PubChem Compound5325915
PDB IDNot Available
ChEBI ID87625
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceIsaac, I.; Aizel, G.; Stasik, I.; Wadouachi, A.; Beaupere, D. A new efficient access to glycono 1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system. Synlett (1998), (5), 475-476.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [PubMed:1192581 ]