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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:07 UTC

Update Date

2023-02-21 17:18:43 UTC

HMDB ID

HMDB0029387

Secondary Accession Numbers

HMDB29387

Metabolite Identification

Common Name

L-3-Aminodihydro-2(3H)-furanone

Description

L-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Aminobutan-4-olide	ChEBI
alpha-Amino-gamma-butyrolactone	ChEBI
Hsl	ChEBI
HSLS	ChEBI
a-Amino-g-butyrolactone	Generator
Α-amino-γ-butyrolactone	Generator
Homoserine lactone hydrochloride, (S)-isomer	MeSH, HMDB
Homoserine lactone, (S)-isomer	MeSH, HMDB
Homoserine lactone hydrobromide	MeSH, HMDB
Homoserine lactone	MeSH, HMDB

Chemical Formula

C₄H₇NO₂

Average Molecular Weight

101.1039

Monoisotopic Molecular Weight

101.047678473

IUPAC Name

3-aminooxolan-2-one

Traditional Name

HSLs

CAS Registry Number

Not Available

SMILES

NC1CCOC1=O

InChI Identifier

InChI=1S/C4H7NO2/c5-3-1-2-7-4(3)6/h3H,1-2,5H2

InChI Key

QJPWUUJVYOJNMH-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

primary amino compound (CHEBI:17289 )
butan-4-olide (CHEBI:17289 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029387)
Cytoplasm (HMDB: HMDB0029387)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029387)

Source

Endogenous

Endogenous (HMDB: HMDB0029387)

Plant

Fabaceae (HMDB: HMDB0029387)

Exogenous

Food

Food (HMDB: HMDB0029387)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0029387)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	695 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-0.9	ChemAxon
logS	0.84	ALOGPS
pKa (Strongest Basic)	7.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	23.41 m³·mol⁻¹	ChemAxon
Polarizability	9.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	118.513	31661259
DarkChem	[M-H]-	112.583	31661259
DeepCCS	[M+H]+	130.448	30932474
DeepCCS	[M-H]-	127.688	30932474
DeepCCS	[M-2H]-	164.0	30932474
DeepCCS	[M+Na]+	138.659	30932474
AllCCS	[M+H]+	121.8	32859911
AllCCS	[M+H-H2O]+	116.8	32859911
AllCCS	[M+NH4]+	126.5	32859911
AllCCS	[M+Na]+	127.8	32859911
AllCCS	[M-H]-	116.6	32859911
AllCCS	[M+Na-2H]-	119.7	32859911
AllCCS	[M+HCOO]-	123.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-3-Aminodihydro-2(3H)-furanone	NC1CCOC1=O	1881.7	Standard polar	33892256
L-3-Aminodihydro-2(3H)-furanone	NC1CCOC1=O	1071.8	Standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone	NC1CCOC1=O	1158.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-3-Aminodihydro-2(3H)-furanone,1TMS,isomer #1	C[Si](C)(C)NC1CCOC1=O	1278.8	Semi standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,1TMS,isomer #1	C[Si](C)(C)NC1CCOC1=O	1228.6	Standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,2TMS,isomer #1	C[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C	1411.8	Semi standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,2TMS,isomer #1	C[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C	1426.7	Standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCOC1=O	1507.7	Semi standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CCOC1=O	1463.6	Standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C(C)(C)C	1810.3	Semi standard non polar	33892256
L-3-Aminodihydro-2(3H)-furanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CCOC1=O)[Si](C)(C)C(C)(C)C	1905.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone EI-B (Non-derivatized)	splash10-0uk9-0950000000-03048a23c7fb90226a53	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone EI-B (Non-derivatized)	splash10-0uk9-0950000000-03048a23c7fb90226a53	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-b9d5d3a95eb0f3d817b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Aminodihydro-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Positive-QTOF	splash10-0udi-5900000000-bebe5f86885084916992	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Positive-QTOF	splash10-0zfr-9200000000-ea641bb623272ddad942	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Positive-QTOF	splash10-0006-9000000000-4265b936b19415f968fa	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Negative-QTOF	splash10-0udi-1900000000-4f2b97073c445663557a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Negative-QTOF	splash10-0zfr-9300000000-691a47924bf6a5d4fcc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Negative-QTOF	splash10-0zml-9000000000-cb080a7af4bdb51b5c2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Positive-QTOF	splash10-0zmi-9500000000-73ccafe0825e00830713	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Positive-QTOF	splash10-0a4i-9100000000-e2e4ad1a4aaa53d5e6ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Positive-QTOF	splash10-0a4u-9000000000-0535253a493b487421bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 10V, Negative-QTOF	splash10-0udi-5900000000-dcbd9472bd7826d8ab9b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 20V, Negative-QTOF	splash10-0piu-9200000000-c15fdf2019bc2c67746b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Aminodihydro-2(3H)-furanone 40V, Negative-QTOF	splash10-0006-9000000000-6f1e0fd9ac45551fad9d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73509

PDB ID

Not Available

ChEBI ID

17289

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L-3-Aminodihydro-2(3H)-furanone (HMDB0029387)

MOL for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

3D MOL for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

3D SDF for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

3D-SDF for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

PDB for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

3D PDB for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

SMILES for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

INCHI for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

Structure for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

3D Structure for HMDB0029387 (L-3-Aminodihydro-2(3H)-furanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra