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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:56 UTC

Update Date

2023-02-21 17:16:25 UTC

HMDB ID

HMDB0002523

Secondary Accession Numbers

HMDB02523

Metabolite Identification

Common Name

Oxolan-3-one

Description

Oxolan-3-one belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Oxolan-3-one 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 oxolan-3-one a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Oxolan-3-one.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Oxotetrahydrofuran	HMDB
dihydro-3(2H)-Furanone	HMDB
Dihydrofuran-3-one	HMDB

Chemical Formula

C₄H₆O₂

Average Molecular Weight

86.0892

Monoisotopic Molecular Weight

86.036779436

IUPAC Name

oxolan-3-one

Traditional Name

dihydrofuran-3-one

CAS Registry Number

22929-52-8

SMILES

O=C1CCOC1

InChI Identifier

InChI=1S/C4H6O2/c5-4-1-2-6-3-4/h1-3H2

InChI Key

JLPJFSCQKHRSQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

3-furanone
Tetrahydrofuran
Cyclic ketone
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0002523)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	519 g/L	ALOGPS
logP	-0.77	ALOGPS
logP	-0.13	ChemAxon
logS	0.78	ALOGPS
pKa (Strongest Acidic)	17.26	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.79 m³·mol⁻¹	ChemAxon
Polarizability	8.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	114.882	31661259
DarkChem	[M-H]-	109.24	31661259
DeepCCS	[M+H]+	123.51	30932474
DeepCCS	[M-H]-	121.609	30932474
DeepCCS	[M-2H]-	156.986	30932474
DeepCCS	[M+Na]+	131.47	30932474
AllCCS	[M+H]+	116.9	32859911
AllCCS	[M+H-H2O]+	111.7	32859911
AllCCS	[M+NH4]+	121.8	32859911
AllCCS	[M+Na]+	123.2	32859911
AllCCS	[M-H]-	117.8	32859911
AllCCS	[M+Na-2H]-	121.5	32859911
AllCCS	[M+HCOO]-	125.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxolan-3-one	O=C1CCOC1	1261.4	Standard polar	33892256
Oxolan-3-one	O=C1CCOC1	752.1	Standard non polar	33892256
Oxolan-3-one	O=C1CCOC1	767.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxolan-3-one,1TMS,isomer #1	C[Si](C)(C)OC1=COCC1	1041.1	Semi standard non polar	33892256
Oxolan-3-one,1TMS,isomer #1	C[Si](C)(C)OC1=COCC1	1113.0	Standard non polar	33892256
Oxolan-3-one,1TMS,isomer #1	C[Si](C)(C)OC1=COCC1	1301.4	Standard polar	33892256
Oxolan-3-one,1TMS,isomer #2	C[Si](C)(C)OC1=CCOC1	1028.6	Semi standard non polar	33892256
Oxolan-3-one,1TMS,isomer #2	C[Si](C)(C)OC1=CCOC1	1056.7	Standard non polar	33892256
Oxolan-3-one,1TMS,isomer #2	C[Si](C)(C)OC1=CCOC1	1430.9	Standard polar	33892256
Oxolan-3-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=COCC1	1253.6	Semi standard non polar	33892256
Oxolan-3-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=COCC1	1286.6	Standard non polar	33892256
Oxolan-3-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=COCC1	1501.8	Standard polar	33892256
Oxolan-3-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCOC1	1239.9	Semi standard non polar	33892256
Oxolan-3-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCOC1	1238.1	Standard non polar	33892256
Oxolan-3-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCOC1	1594.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxolan-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-6bd9ce1a931567e1a3c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxolan-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxolan-3-one 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 - Oxolan-3-one 10V, Positive-QTOF	splash10-00kr-9000000000-5da5eed3d0cef39e111b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 20V, Positive-QTOF	splash10-014r-9000000000-9421cd516498f73625c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 40V, Positive-QTOF	splash10-05mx-9000000000-b5df4764b83c47f8ffa7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 10V, Negative-QTOF	splash10-000i-9000000000-e518d36e5c3a96d352d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 20V, Negative-QTOF	splash10-000i-9000000000-e248a8d271e76f8e3620	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 40V, Negative-QTOF	splash10-0a4i-9000000000-ad8a22266f418dcac3df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 10V, Positive-QTOF	splash10-014u-9000000000-b0876187a6dbde032ab5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 20V, Positive-QTOF	splash10-00kf-9000000000-2a42cec2791b867b19a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 40V, Positive-QTOF	splash10-0006-9000000000-e6a74265a10064561eab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 10V, Negative-QTOF	splash10-000l-9000000000-bed45fc6374cfd503a78	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 20V, Negative-QTOF	splash10-00kf-9000000000-08e7e44813a583e61cdb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxolan-3-one 40V, Negative-QTOF	splash10-0006-9000000000-6dcb2d8d2a0bb3439213	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB023023

KNApSAcK ID

Not Available

Chemspider ID

461367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6710

PubChem Compound

529392

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Weiland, J. H. Sperna. The chemistry of 3-oxotetrahydrofurans. II. Cyclization of 2-alkoxyethyl diazomethyl ketones. Recueil des Travaux Chimiques des Pays-Bas (1964), 84(1), 81-93.

Material Safety Data Sheet (MSDS)

Not Available

General References

Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
Chalmers RA: Organic acids in urine of patients with congenital lactic acidoses: an aid to differential diagnosis. J Inherit Metab Dis. 1984;7 Suppl 1:79-89. [PubMed:6434850 ]

Showing metabocard for Oxolan-3-one (HMDB0002523)

MOL for HMDB0002523 (Oxolan-3-one)

3D MOL for HMDB0002523 (Oxolan-3-one)

3D SDF for HMDB0002523 (Oxolan-3-one)

3D-SDF for HMDB0002523 (Oxolan-3-one)

PDB for HMDB0002523 (Oxolan-3-one)

3D PDB for HMDB0002523 (Oxolan-3-one)

SMILES for HMDB0002523 (Oxolan-3-one)

INCHI for HMDB0002523 (Oxolan-3-one)

Structure for HMDB0002523 (Oxolan-3-one)

3D Structure for HMDB0002523 (Oxolan-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra