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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

2012-09-12 01:46:55 UTC

Update Date

2023-02-21 17:28:01 UTC

HMDB ID

HMDB0040246

Secondary Accession Numbers

HMDB40246

Metabolite Identification

Common Name

3,5,5-Trimethyl-2-cyclopenten-1-one

Description

3,5,5-Trimethyl-2-cyclopenten-1-one 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. 3,5,5-Trimethyl-2-cyclopenten-1-one has been detected, but not quantified in, herbs and spices. This could make 3,5,5-trimethyl-2-cyclopenten-1-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,5,5-Trimethyl-2-cyclopenten-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
3,5,5-Trimethyl-2-cyclopentenone	HMDB
3,5,5-Trimethyl-cyclopent-2-en-1-one	HMDB

Chemical Formula

C₈H₁₂O

Average Molecular Weight

124.1803

Monoisotopic Molecular Weight

124.088815006

IUPAC Name

3,5,5-trimethylcyclopent-2-en-1-one

Traditional Name

3,5,5-trimethylcyclopent-2-en-1-one

CAS Registry Number

24156-95-4

SMILES

CC1=CC(=O)C(C)(C)C1

InChI Identifier

InChI=1S/C8H12O/c1-6-4-7(9)8(2,3)5-6/h4H,5H2,1-3H3

InChI Key

AVXVDNJFGZNVAB-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
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040246)
Cytoplasm (HMDB: HMDB0040246)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040246)

Source

Exogenous

Food

Food (HMDB: HMDB0040246)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0040246)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040246)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	173.02 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1478 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.217 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.87 g/L	ALOGPS
logP	1.56	ALOGPS
logP	2.38	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	18.25	ChemAxon
pKa (Strongest Basic)	-4.7	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	38.1 m³·mol⁻¹	ChemAxon
Polarizability	14.41 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]+	129.796	31661259
DarkChem	[M-H]-	123.578	31661259
DeepCCS	[M+H]+	133.21	30932474
DeepCCS	[M-H]-	130.617	30932474
DeepCCS	[M-2H]-	166.864	30932474
DeepCCS	[M+Na]+	142.011	30932474
AllCCS	[M+H]+	123.0	32859911
AllCCS	[M+H-H2O]+	118.3	32859911
AllCCS	[M+NH4]+	127.3	32859911
AllCCS	[M+Na]+	128.6	32859911
AllCCS	[M-H]-	125.0	32859911
AllCCS	[M+Na-2H]-	127.2	32859911
AllCCS	[M+HCOO]-	129.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-2-cyclopenten-1-one	CC1=CC(=O)C(C)(C)C1	1406.1	Standard polar	33892256
3,5,5-Trimethyl-2-cyclopenten-1-one	CC1=CC(=O)C(C)(C)C1	983.7	Standard non polar	33892256
3,5,5-Trimethyl-2-cyclopenten-1-one	CC1=CC(=O)C(C)(C)C1	945.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-06di-9300000000-981a2c10cb9269537395	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-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 - 3,5,5-Trimethyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-004i-0900000000-7a5a055d030f5d030995	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-056r-7900000000-7ca0b0081cb81392f498	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0a4r-9000000000-1571b560b9ff46197a93	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-00di-0900000000-9be8563f3d0e590abd0d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-00di-0900000000-d6349807a37e390a9774	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-0592-9600000000-c91b7a42db53942192bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-00di-0900000000-9da3c432fb05c315dc1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-00di-0900000000-9da3c432fb05c315dc1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-01b9-9500000000-709482cc84c59abf5895	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-056r-9800000000-b043dee66d6aa65c86be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-056u-9000000000-207aac20990919c14851	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-000f-9000000000-9005b3c846bba7247e25	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

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

FDB019961

KNApSAcK ID

C00058043

Chemspider ID

29898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

32240

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1130541

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 3,5,5-Trimethyl-2-cyclopenten-1-one (HMDB0040246)

MOL for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

3D MOL for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

3D SDF for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

3D-SDF for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

PDB for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

3D PDB for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

SMILES for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

INCHI for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

Structure for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

3D Structure for HMDB0040246 (3,5,5-Trimethyl-2-cyclopenten-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra