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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

2021-09-23 23:53:10 UTC

Update Date

2021-09-23 23:53:10 UTC

HMDB ID

HMDB0303163

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Hydroxy-3-methyl-2-cyclopenten-1-one

Description

2-hydroxy-3-methyl-2-cyclopenten-1-one, also known as cyclotene, is a member of the class of compounds known as cyclic ketones. Cyclic ketones are organic compounds containing a ketone that is conjugated to a cyclic moiety. 2-hydroxy-3-methyl-2-cyclopenten-1-one is soluble (in water) and a very weakly acidic compound (based on its pKa). 2-hydroxy-3-methyl-2-cyclopenten-1-one is a caramel, maple, and maple syrup tasting compound and can be found in a number of food items such as pepper (c. annuum), green bell pepper, red bell pepper, and yellow bell pepper, which makes 2-hydroxy-3-methyl-2-cyclopenten-1-one a potential biomarker for the consumption of these food products.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-1-methylcyclopenten-3-one	MeSH
Cyclotene	MeSH

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

2-hydroxy-3-methylcyclopent-2-en-1-one

Traditional Name

cyclotene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3

InChI Key

CFAKWWQIUFSQFU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Enol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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
logP	-0.19	ALOGPS
logP	0.77	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.99 m³·mol⁻¹	ChemAxon
Polarizability	11.5 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
AllCCS	[M+H]+	124.084	32859911
AllCCS	[M+H-H2O]+	119.288	32859911
AllCCS	[M+Na]+	129.855	32859911
AllCCS	[M+NH4]+	128.562	32859911
AllCCS	[M-H]-	121.74	32859911
AllCCS	[M+Na-2H]-	124.361	32859911
AllCCS	[M+HCOO]-	127.275	32859911
DeepCCS	[M+H]+	125.213	30932474
DeepCCS	[M-H]-	121.756	30932474
DeepCCS	[M-2H]-	158.901	30932474
DeepCCS	[M+Na]+	134.018	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1341.6	Semi standard non polar	33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1394.5	Standard non polar	33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1364.9	Standard polar	33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1824.5	Semi standard non polar	33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1701.3	Standard non polar	33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1670.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-a5794263e8fc3b77a0da	2016-09-22	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9300000000-bb5ced3db053bc297e39	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-03di-2900000000-443c9e416dd135f377f8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-03di-9600000000-ff69e503b03cae6a7800	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0zfr-9000000000-3d372ea8b42cf1712eca	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-03di-0900000000-927a6165f31587a98747	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-03di-3900000000-a9c6bddefe3fe4bc5396	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-0f6x-9000000000-dc99abf78fed8af7f6dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-03di-9500000000-c5ab7a62fd90435027a3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-014r-9000000000-ce380cfd591088691e0d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0006-9000000000-70fec2d9bc8407f4526d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-01q9-9600000000-ef24c7460c2dd9567fd5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-03di-9600000000-453c8a59b6989e49e622	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-0006-9000000000-f374341928e04208d34d	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart 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

FDB008103

KNApSAcK ID

Not Available

Chemspider ID

6408

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2-Hydroxy-3-methyl-2-cyclopenten-1-one (HMDB0303163)

MOL for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

3D MOL for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

3D SDF for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

3D-SDF for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

PDB for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

3D PDB for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

SMILES for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

INCHI for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

Structure for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

3D Structure for HMDB0303163 (2-Hydroxy-3-methyl-2-cyclopenten-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra