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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:57 UTC

Update Date

2023-02-21 17:20:46 UTC

HMDB ID

HMDB0031541

Secondary Accession Numbers

HMDB31541

Metabolite Identification

Common Name

3-Methyl-2-cyclohexen-1-one

Description

3-Methyl-2-cyclohexen-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3-Methyl-2-cyclohexen-1-one is a caramel, cherry, and nut tasting compound. Based on a literature review very few articles have been published on 3-Methyl-2-cyclohexen-1-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-Methyl-2-cyclohexene-1-one	HMDB
3-Methyl-2-cyclohexenone	HMDB
3-Methyl-2-cyclohexenone-1	HMDB
3-Methylcyclohex-2-en-1-one	HMDB, MeSH
FEMA 3360	HMDB
Ghl.PD_Mitscher_leg0.699	HMDB
MCH	HMDB
Methylcyclohexenone	HMDB
Seudenone	HMDB
MCH CPD	MeSH
3-Methyl-2-cyclohexen-1-one	MeSH

Chemical Formula

C₇H₁₀O

Average Molecular Weight

110.1537

Monoisotopic Molecular Weight

110.073164942

IUPAC Name

3-methylcyclohex-2-en-1-one

Traditional Name

2-cyclohexen-1-one, 3-methyl-

CAS Registry Number

1193-18-6

SMILES

CC1=CC(=O)CCC1

InChI Identifier

InChI=1S/C7H10O/c1-6-3-2-4-7(8)5-6/h5H,2-4H2,1H3

InChI Key

IITQJMYAYSNIMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031541)
Cytoplasm (HMDB: HMDB0031541)

Source

Endogenous

Endogenous (HMDB: HMDB0031541)

Exogenous

Food

Food (HMDB: HMDB0031541)

Exogenous (HMDB: HMDB0031541)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031541)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-21 °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	8.09 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.73	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	19.1	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.62 m³·mol⁻¹	ChemAxon
Polarizability	12.51 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]+	125.312	31661259
DarkChem	[M-H]-	119.194	31661259
DeepCCS	[M+H]+	126.669	30932474
DeepCCS	[M-H]-	124.398	30932474
DeepCCS	[M-2H]-	160.607	30932474
DeepCCS	[M+Na]+	135.438	30932474
AllCCS	[M+H]+	121.9	32859911
AllCCS	[M+H-H2O]+	116.9	32859911
AllCCS	[M+NH4]+	126.5	32859911
AllCCS	[M+Na]+	127.8	32859911
AllCCS	[M-H]-	123.8	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-cyclohexen-1-one	CC1=CC(=O)CCC1	1576.8	Standard polar	33892256
3-Methyl-2-cyclohexen-1-one	CC1=CC(=O)CCC1	975.2	Standard non polar	33892256
3-Methyl-2-cyclohexen-1-one	CC1=CC(=O)CCC1	1021.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-cyclohexen-1-one,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CCC1	1166.1	Semi standard non polar	33892256
3-Methyl-2-cyclohexen-1-one,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CCC1	1176.4	Standard non polar	33892256
3-Methyl-2-cyclohexen-1-one,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CCC1	1394.7	Semi standard non polar	33892256
3-Methyl-2-cyclohexen-1-one,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CCC1	1375.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9100000000-1f14f50705992aa13677	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-2-cyclohexen-1-one EI-B (Non-derivatized)	splash10-001i-9100000000-1f14f50705992aa13677	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hhc-9000000000-04df37fc0db905815eec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-cyclohexen-1-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 - 3-Methyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-03di-2900000000-cca81ab2bedb68bce3f0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 20V, Positive-QTOF	splash10-03dl-9600000000-00a40eb8708d4a555905	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 40V, Positive-QTOF	splash10-0fr6-9000000000-250c27e7e382080efd08	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 10V, Negative-QTOF	splash10-0a4i-0900000000-78ee914e3e8d05f6bb08	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 20V, Negative-QTOF	splash10-0a4i-1900000000-b3c47a5b842e03a8b1de	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 40V, Negative-QTOF	splash10-052f-9100000000-93eade932b987d1bcbe8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 10V, Negative-QTOF	splash10-0a4i-0900000000-793dd728af605c3456d0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 20V, Negative-QTOF	splash10-0a4i-2900000000-78b0d1d441bcec4d99b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 40V, Negative-QTOF	splash10-0aou-9500000000-e63a3ea6ef4ce3b9c8e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 10V, Positive-QTOF	splash10-03di-6900000000-88e308425a9ba051e483	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 20V, Positive-QTOF	splash10-00kf-9000000000-d82d3bb51673016cec57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclohexen-1-one 40V, Positive-QTOF	splash10-014l-9000000000-fb77fef4cd4e147649ea	2021-09-24	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details

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

FDB008151

KNApSAcK ID

C00011600

Chemspider ID

13855

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14511

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

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

Showing metabocard for 3-Methyl-2-cyclohexen-1-one (HMDB0031541)

MOL for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

3D MOL for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

3D SDF for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

3D-SDF for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

PDB for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

3D PDB for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

SMILES for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

INCHI for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

Structure for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

3D Structure for HMDB0031541 (3-Methyl-2-cyclohexen-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra