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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:00 UTC

Update Date

2023-02-21 17:21:24 UTC

HMDB ID

HMDB0031859

Secondary Accession Numbers

HMDB31859

Metabolite Identification

Common Name

Norfuraneol

Description

Norfuraneol, also known as 4Hm-furanone, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Norfuraneol is a sweet, bready, and candy tasting compound. Norfuraneol has been detected, but not quantified in, several different foods, such as beer, blackberries (Rubus), evergreen blackberries (Rubus laciniatus), and fruits. This could make norfuraneol a potential biomarker for the consumption of these foods. Norfuraneol 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 Norfuraneol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-5-methyl-3(2H)-furanone	MeSH
4-Hydroxy-5-methylfuran-3(2H)-one	MeSH
4Hm-Furanone	MeSH
5-Methyl-4-hydroxy-3(2H)-furanone	MeSH
4-Hydroxy-5-methyl-2,3-dihydrofuran-3-one	HMDB
4-Hydroxy-5-methyl-3-furanone	HMDB
Norfuraneol	MeSH

Chemical Formula

C₅H₆O₃

Average Molecular Weight

114.0993

Monoisotopic Molecular Weight

114.031694058

IUPAC Name

4-hydroxy-5-methyl-2,3-dihydrofuran-3-one

Traditional Name

4-hydroxy-5-methyl-2H-furan-3-one

CAS Registry Number

19322-27-1

SMILES

CC1=C(O)C(=O)CO1

InChI Identifier

InChI=1S/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3

InChI Key

DLVYTANECMRFGX-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
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

cyclic ketone (CHEBI:74456 )
furans (CHEBI:74456 )
enol (CHEBI:74456 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031859)
Cytoplasm (HMDB: HMDB0031859)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031859)

Source

Endogenous

Endogenous (HMDB: HMDB0031859)

Plant

Plant (HMDB: HMDB0031859)

Exogenous

Food

Food (HMDB: HMDB0031859)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Fruit

Fruits (FooDB: FOOD00871)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Exogenous (HMDB: HMDB0031859)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031859)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	126.6 - 127.5 °C	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	616 g/L	ALOGPS
logP	-0.83	ALOGPS
logP	-0.36	ChemAxon
logS	0.73	ALOGPS
pKa (Strongest Acidic)	6.88	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	28.8 m³·mol⁻¹	ChemAxon
Polarizability	10.5 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
DeepCCS	[M+H]+	128.121	30932474
DeepCCS	[M-H]-	125.798	30932474
DeepCCS	[M-2H]-	162.118	30932474
DeepCCS	[M+Na]+	136.837	30932474
AllCCS	[M+H]+	122.9	32859911
AllCCS	[M+H-H2O]+	118.0	32859911
AllCCS	[M+NH4]+	127.5	32859911
AllCCS	[M+Na]+	128.8	32859911
AllCCS	[M-H]-	119.2	32859911
AllCCS	[M+Na-2H]-	121.7	32859911
AllCCS	[M+HCOO]-	124.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.41 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4525 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1386.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	412.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	278.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	465.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	421.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	841.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	299.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1119.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	294.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	639.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	346.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	177.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norfuraneol	CC1=C(O)C(=O)CO1	2037.5	Standard polar	33892256
Norfuraneol	CC1=C(O)C(=O)CO1	975.6	Standard non polar	33892256
Norfuraneol	CC1=C(O)C(=O)CO1	1042.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norfuraneol,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CO1	1143.6	Semi standard non polar	33892256
Norfuraneol,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=CO1	1197.1	Semi standard non polar	33892256
Norfuraneol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CO1	1247.8	Semi standard non polar	33892256
Norfuraneol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CO1	1309.9	Standard non polar	33892256
Norfuraneol,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CO1	1395.2	Semi standard non polar	33892256
Norfuraneol,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CO1	1504.6	Semi standard non polar	33892256
Norfuraneol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CO1	1742.6	Semi standard non polar	33892256
Norfuraneol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CO1	1730.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norfuraneol GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-c057722961052e7db7cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfuraneol GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-9500000000-44f15f27c3c3c1813bd6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfuraneol 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 - Norfuraneol 10V, Positive-QTOF	splash10-014i-2900000000-bc4ceda0d7268fec7380	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 20V, Positive-QTOF	splash10-014j-9700000000-3cc94b2bfed7a5fbb135	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 40V, Positive-QTOF	splash10-054p-9000000000-4fda2f9ca6d91ed81b4b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 10V, Negative-QTOF	splash10-03di-1900000000-0a8bbbe75f7fe8274a46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 20V, Negative-QTOF	splash10-03di-4900000000-b1f26dce36a045259cdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 40V, Negative-QTOF	splash10-0006-9000000000-4c53903862f4136368a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 10V, Positive-QTOF	splash10-066u-9300000000-fb42cca00dbe8013dab4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 20V, Positive-QTOF	splash10-0006-9000000000-923a600b3a1f5143ac69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 40V, Positive-QTOF	splash10-0006-9000000000-856565bd4acb22def6d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 10V, Negative-QTOF	splash10-022c-9200000000-b403c75353e48c7f21c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 20V, Negative-QTOF	splash10-0a4i-9000000000-193d36314c6367d66750	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfuraneol 40V, Negative-QTOF	splash10-052f-9000000000-29f17cdfee419ec3fa27	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

FDB008543

KNApSAcK ID

Not Available

Chemspider ID

3757733

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4564493

PDB ID

Not Available

ChEBI ID

74456

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 Norfuraneol (HMDB0031859)

MOL for HMDB0031859 (Norfuraneol)

3D MOL for HMDB0031859 (Norfuraneol)

3D SDF for HMDB0031859 (Norfuraneol)

3D-SDF for HMDB0031859 (Norfuraneol)

PDB for HMDB0031859 (Norfuraneol)

3D PDB for HMDB0031859 (Norfuraneol)

SMILES for HMDB0031859 (Norfuraneol)

INCHI for HMDB0031859 (Norfuraneol)

Structure for HMDB0031859 (Norfuraneol)

3D Structure for HMDB0031859 (Norfuraneol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra