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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

2012-09-11 17:41:42 UTC

Update Date

2023-02-21 17:20:07 UTC

HMDB ID

HMDB0031222

Secondary Accession Numbers

HMDB31222

Metabolite Identification

Common Name

3-Ethyl-1,2-cyclopentanedione

Description

3-Ethyl-1,2-cyclopentanedione 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-Ethyl-1,2-cyclopentanedione 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 3-ethyl-1,2-cyclopentanedione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Ethyl-1,2-cyclopentanedione.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Ethyl-2-hydroxy-2-cyclopenten-1-one, 9ci	HMDB
FEMA 3152	HMDB

Chemical Formula

C₇H₁₀O₂

Average Molecular Weight

126.1531

Monoisotopic Molecular Weight

126.068079564

IUPAC Name

3-ethylcyclopentane-1,2-dione

Traditional Name

3-ethylcyclopentane-1,2-dione

CAS Registry Number

Not Available

SMILES

CCC1CCC(=O)C1=O

InChI Identifier

InChI=1S/C7H10O2/c1-2-5-3-4-6(8)7(5)9/h5H,2-4H2,1H3

InChI Key

RRVYBPVLSILURP-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

Not Available

Ingestion (HMDB: HMDB0031222)

Source

Endogenous

Endogenous (HMDB: HMDB0031222)

Plant

Coffea (HMDB: HMDB0031222)

Exogenous

Food

Food (HMDB: HMDB0031222)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031222)

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
Water Solubility	19.2 g/L	ALOGPS
logP	1.15	ALOGPS
logP	1.88	ChemAxon
logS	-0.82	ALOGPS
pKa (Strongest Acidic)	16.17	ChemAxon
pKa (Strongest Basic)	-8.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33.57 m³·mol⁻¹	ChemAxon
Polarizability	13.25 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]+	127.317	31661259
DarkChem	[M-H]-	124.388	31661259
DeepCCS	[M+H]+	132.644	30932474
DeepCCS	[M-H]-	129.827	30932474
DeepCCS	[M-2H]-	166.411	30932474
DeepCCS	[M+Na]+	141.19	30932474
AllCCS	[M+H]+	127.0	32859911
AllCCS	[M+H-H2O]+	122.4	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.6	32859911
AllCCS	[M-H]-	126.9	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-1,2-cyclopentanedione	CCC1CCC(=O)C1=O	1724.5	Standard polar	33892256
3-Ethyl-1,2-cyclopentanedione	CCC1CCC(=O)C1=O	1066.2	Standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione	CCC1CCC(=O)C1=O	1100.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-1,2-cyclopentanedione,1TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(=O)CC1	1259.7	Semi standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(=O)CC1	1225.2	Standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TMS,isomer #2	CCC1CC=C(O[Si](C)(C)C)C1=O	1256.0	Semi standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TMS,isomer #2	CCC1CC=C(O[Si](C)(C)C)C1=O	1213.3	Standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,2TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1424.1	Semi standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,2TMS,isomer #1	CCC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1501.3	Standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1	1510.7	Semi standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1	1435.3	Standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CCC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O	1483.8	Semi standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CCC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O	1433.4	Standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1896.0	Semi standard non polar	33892256
3-Ethyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CCC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1784.0	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-Ethyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-054p-9100000000-1172c36a950a14262566	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 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-Ethyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-004i-3900000000-8fefffd593073694c2d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-0kdl-9300000000-70073cad831f3a1fba2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-0006-9000000000-676e2a3bd08178e4d541	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-004i-0900000000-2490af012db8f66ad348	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-004i-2900000000-2641de90462541ba6d6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-00kf-9000000000-6245bd0f2ccbe024d8c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-004i-0900000000-dd34846512c5616c2cd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-004l-9600000000-a883119646c75cbb07d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-00kf-9000000000-a11090406ef2febd4a69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-056r-6900000000-fb827ea67262d78b276d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-0a4i-9000000000-d668da49d3e434695497	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-052f-9000000000-8dd745963540fe2a9d20	2021-09-23	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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

FDB003246

KNApSAcK ID

Not Available

Chemspider ID

102588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114535

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-Ethyl-1,2-cyclopentanedione (HMDB0031222)

MOL for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

3D MOL for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

3D SDF for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

3D-SDF for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

PDB for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

3D PDB for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

SMILES for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

INCHI for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

Structure for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

3D Structure for HMDB0031222 (3-Ethyl-1,2-cyclopentanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra