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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:07 UTC
Update Date2021-09-14 15:20:34 UTC
HMDB IDHMDB0029387
Secondary Accession Numbers
  • HMDB29387
Metabolite Identification
Common NameL-3-Aminodihydro-2(3H)-furanone
DescriptionL-3-Aminodihydro-2(3H)-furanone, also known as 2-aminobutan-4-olide or Hsl, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. L-3-Aminodihydro-2(3H)-furanone has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make L-3-aminodihydro-2(3H)-furanone a potential biomarker for the consumption of these foods. L-3-Aminodihydro-2(3H)-furanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-3-Aminodihydro-2(3H)-furanone.
Structure
Data?1582753411
Synonyms
ValueSource
2-Aminobutan-4-olideChEBI
alpha-Amino-gamma-butyrolactoneChEBI
HslChEBI
HSLSChEBI
a-Amino-g-butyrolactoneGenerator
Α-amino-γ-butyrolactoneGenerator
Homoserine lactone hydrochloride, (S)-isomerMeSH, HMDB
Homoserine lactone, (S)-isomerMeSH, HMDB
Homoserine lactone hydrobromideMeSH, HMDB
Homoserine lactoneMeSH, HMDB
Chemical FormulaC4H7NO2
Average Molecular Weight101.1039
Monoisotopic Molecular Weight101.047678473
IUPAC Name3-aminooxolan-2-one
Traditional NameHSLs
CAS Registry NumberNot Available
SMILES
NC1CCOC1=O
InChI Identifier
InChI=1S/C4H7NO2/c5-3-1-2-7-4(3)6/h3H,1-2,5H2
InChI KeyQJPWUUJVYOJNMH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
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 Solubility695 g/LALOGPS
logP10(-1.4) g/LALOGPS
logP10(-0.9) g/LChemAxon
logS10(0.84) g/LALOGPS
pKa (Strongest Basic)7.33ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.41 m³·mol⁻¹ChemAxon
Polarizability9.47 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]+118.51331661259
DarkChem[M-H]-112.58331661259
DeepCCS[M+H]+130.44830932474
DeepCCS[M-H]-127.68830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-3-Aminodihydro-2(3H)-furanoneNC1CCOC1=O1881.7Standard polar33892256
L-3-Aminodihydro-2(3H)-furanoneNC1CCOC1=O1071.8Standard non polar33892256
L-3-Aminodihydro-2(3H)-furanoneNC1CCOC1=O1158.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-3-Aminodihydro-2(3H)-furanone,1TMS,isomer #1C[Si](C)(C)NC1CCOC1=O1278.8Semi standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,1TMS,isomer #1C[Si](C)(C)NC1CCOC1=O1228.6Standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,2TMS,isomer #1C[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C1411.8Semi standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,2TMS,isomer #1C[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C1426.7Standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1CCOC1=O1507.7Semi standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1CCOC1=O1463.6Standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C(C)(C)C1810.3Semi standard non polar33892256
L-3-Aminodihydro-2(3H)-furanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C(C)(C)C1905.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone EI-B (Non-derivatized)splash10-0uk9-0950000000-03048a23c7fb90226a532017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone EI-B (Non-derivatized)splash10-0uk9-0950000000-03048a23c7fb90226a532018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-b9d5d3a95eb0f3d817b02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 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 - L-3-Aminodihydro-2(3H)-furanone 10V, Positive-QTOFsplash10-0udi-5900000000-bebe5f868850849169922016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Positive-QTOFsplash10-0zfr-9200000000-ea641bb623272ddad9422016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Positive-QTOFsplash10-0006-9000000000-4265b936b19415f968fa2016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Negative-QTOFsplash10-0udi-1900000000-4f2b97073c445663557a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Negative-QTOFsplash10-0zfr-9300000000-691a47924bf6a5d4fcc42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Negative-QTOFsplash10-0zml-9000000000-cb080a7af4bdb51b5c2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Positive-QTOFsplash10-0zmi-9500000000-73ccafe0825e008307132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Positive-QTOFsplash10-0a4i-9100000000-e2e4ad1a4aaa53d5e6ef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Positive-QTOFsplash10-0a4u-9000000000-0535253a493b487421bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Negative-QTOFsplash10-0udi-5900000000-dcbd9472bd7826d8ab9b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Negative-QTOFsplash10-0piu-9200000000-c15fdf2019bc2c67746b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Negative-QTOFsplash10-0006-9000000000-6f1e0fd9ac45551fad9d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB000468
KNApSAcK IDC00053321
Chemspider ID66194
KEGG Compound IDC02926
BioCyc IDHOMOSERINE-LACTONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73509
PDB IDNot Available
ChEBI ID17289
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .