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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:10:58 UTC

Update Date

2022-03-07 02:56:17 UTC

HMDB ID

HMDB0039652

Secondary Accession Numbers

HMDB39652

Metabolite Identification

Common Name

2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one

Description

2-Hydroxy-3,4,5-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. 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2-hydroxy-3,4,5-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 2-Hydroxy-3,4,5-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

Not Available

Chemical Formula

C₈H₁₂O₂

Average Molecular Weight

140.1797

Monoisotopic Molecular Weight

140.083729628

IUPAC Name

2-hydroxy-3,4,5-trimethylcyclopent-2-en-1-one

Traditional Name

2-hydroxy-3,4,5-trimethylcyclopent-2-en-1-one

CAS Registry Number

109682-87-3

SMILES

CC1C(C)C(=O)C(O)=C1C

InChI Identifier

InChI=1S/C8H12O2/c1-4-5(2)7(9)8(10)6(4)3/h4-5,10H,1-3H3

InChI Key

RMXYMRMUZJILGN-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039652)

Source

Endogenous

Endogenous (HMDB: HMDB0039652)

Plant

Coffea (HMDB: HMDB0039652)

Exogenous

Food

Food (HMDB: HMDB0039652)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0039652)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0039652)

Role

Biological role

Energy source (HMDB: HMDB0039652)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039652)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039652)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	249.61 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1285 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.641 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	26.5 g/L	ALOGPS
logP	0.62	ALOGPS
logP	1.6	ChemAxon
logS	-0.72	ALOGPS
pKa (Strongest Acidic)	9.42	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	40.11 m³·mol⁻¹	ChemAxon
Polarizability	15.32 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
DeepCCS	[M+H]+	134.734	30932474
DeepCCS	[M-H]-	131.416	30932474
DeepCCS	[M-2H]-	168.727	30932474
DeepCCS	[M+Na]+	144.044	30932474
AllCCS	[M+H]+	129.8	32859911
AllCCS	[M+H-H2O]+	125.4	32859911
AllCCS	[M+NH4]+	134.0	32859911
AllCCS	[M+Na]+	135.2	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	133.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one	CC1C(C)C(=O)C(O)=C1C	1849.7	Standard polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one	CC1C(C)C(=O)C(O)=C1C	1114.3	Standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one	CC1C(C)C(=O)C(O)=C1C	1113.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)C(C)C1C	1263.5	Semi standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=C(C)C1C	1299.4	Semi standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)C1C	1439.0	Semi standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)C1C	1438.7	Standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)C1C	1512.9	Semi standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C)C1C	1536.8	Semi standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-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)=C(C)C1C	1900.1	Semi standard non polar	33892256
2-Hydroxy-3,4,5-trimethyl-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)=C(C)C1C	1905.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-9400000000-108b7894d40aad538844	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one GC-MS (1 TMS) - 70eV, Positive	splash10-01xt-6900000000-83460a2468399fe48b70	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-3,4,5-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 - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-0006-1900000000-0ef4571a50024d8ff76c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-0zfu-9200000000-a5805d901432bbf7f7dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0zfr-9000000000-dfd89b500106994ac37f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-000i-0900000000-e9bed322ffae4a5760d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-000i-2900000000-fa9fc8bdbdcded5754e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-0a4i-9400000000-22129698772ef7a77dec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-000i-0900000000-a5734f49b62679635a5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-000i-1900000000-ef9e68683560cab84a84	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-0a4r-9600000000-a0615647847447c4579f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-0006-5900000000-17710168e8ce4682bf5e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-05od-9500000000-56a9c08a44e6a8afe783	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0a4i-9000000000-b74dfd39caea00887e9b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB019281

KNApSAcK ID

Not Available

Chemspider ID

460798

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

528707

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1697861

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 2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one (HMDB0039652)

MOL for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

3D MOL for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

3D SDF for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

3D-SDF for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

PDB for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

3D PDB for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

SMILES for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

INCHI for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

Structure for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

3D Structure for HMDB0039652 (2-Hydroxy-3,4,5-trimethyl-2-cyclopenten-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra