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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

HMDB0031223

Secondary Accession Numbers

HMDB31223

Metabolite Identification

Common Name

Enol-3-Ethyl-1,2-cyclopentanedione

Description

Enol-3-Ethyl-1,2-cyclopentanedione, also known as 2-hydroxy-3-ethyl-2-cyclopenten-1-one or 2-cyclopenten-1-one, 2-hydroxy-3-ethyl, 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. Based on a literature review very few articles have been published on Enol-3-Ethyl-1,2-cyclopentanedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Cyclopenten-1-one, 2-hydroxy-3-ethyl	HMDB
2-Hydroxy-3-ethyl-2-cyclopenten-1-one	HMDB
2-Hydroxy-3-ethyl-2-cyclopentene-1-one	HMDB
3-Ethyl-2-cyclopenten-2-ol-1-one	HMDB
3-Ethyl-2-hydroxy-2-cyclopenten-1-one	HMDB
3-Ethyl-2-hydroxy-2-cyclopentenone	HMDB
3-Ethyl-2-hydroxycyclopent-2-en-1-one	HMDB

Chemical Formula

C₇H₁₀O₂

Average Molecular Weight

126.1531

Monoisotopic Molecular Weight

126.068079564

IUPAC Name

3-ethyl-2-hydroxycyclopent-2-en-1-one

Traditional Name

3-ethyl-2-hydroxycyclopent-2-en-1-one

CAS Registry Number

21835-01-8

SMILES

CCC1=C(O)C(=O)CC1

InChI Identifier

InChI=1S/C7H10O2/c1-2-5-3-4-6(8)7(5)9/h9H,2-4H2,1H3

InChI Key

JHWFWLUAUPZUCP-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

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031223)
Cytoplasm (HMDB: HMDB0031223)

Source

Endogenous

Endogenous (HMDB: HMDB0031223)

Exogenous

Food

Food (HMDB: HMDB0031223)

Exogenous (HMDB: HMDB0031223)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	38 - 40 °C	Not Available
Boiling Point	78.00 to 80.00 °C. @ 4.00 mm Hg	The Good Scents Company Information System
Water Solubility	2878 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.080 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	45.6 g/L	ALOGPS
logP	0.38	ALOGPS
logP	1.21	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Acidic)	9.39	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	1	ChemAxon
Refractivity	35.59 m³·mol⁻¹	ChemAxon
Polarizability	13.4 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]+	129.406	30932474
DeepCCS	[M-H]-	125.705	30932474
DeepCCS	[M-2H]-	163.09	30932474
DeepCCS	[M+Na]+	138.272	30932474
AllCCS	[M+H]+	127.8	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	132.1	32859911
AllCCS	[M+Na]+	133.3	32859911
AllCCS	[M-H]-	126.7	32859911
AllCCS	[M+Na-2H]-	128.9	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.13 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0011 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1459.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	446.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	396.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	771.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	303.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1021.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	479.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	150.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Enol-3-Ethyl-1,2-cyclopentanedione	CCC1=C(O)C(=O)CC1	1804.0	Standard polar	33892256
Enol-3-Ethyl-1,2-cyclopentanedione	CCC1=C(O)C(=O)CC1	1057.7	Standard non polar	33892256
Enol-3-Ethyl-1,2-cyclopentanedione	CCC1=C(O)C(=O)CC1	1090.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Enol-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
Enol-3-Ethyl-1,2-cyclopentanedione,1TMS,isomer #2	CCC1=C(O)C(O[Si](C)(C)C)=CC1	1320.5	Semi standard non polar	33892256
Enol-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
Enol-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
Enol-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
Enol-3-Ethyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CCC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CC1	1527.5	Semi standard non polar	33892256
Enol-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
Enol-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 - Enol-3-Ethyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-014m-9100000000-4c96de4183295223b308	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione GC-MS (1 TMS) - 70eV, Positive	splash10-0ac3-9800000000-af1b2f46693bbe903ecf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enol-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 - Enol-3-Ethyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-004i-2900000000-e7cb6321e4fc0240e515	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-0ufr-9200000000-bc850b903993994df79e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-0006-9000000000-5449afc3aee39be7dda8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-004i-0900000000-3bd6dd8c57f3deaa7f05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-004i-2900000000-ad221cdf3fd85141a858	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-05ow-9100000000-c6ad0272de03fd332cc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-004i-3900000000-a9f5cceccf6f50edcc3b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-004l-9200000000-b2e6910eef9e76f81efd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-00r6-9200000000-26729be1a3bedda96798	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-004i-3900000000-e621512dc8b09f9c5f4e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-001i-9000000000-fa2947315e35a1dca253	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enol-3-Ethyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-000f-9000000000-652bbfbe7d97be98e08f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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, 1000 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

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+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

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

FDB003247

KNApSAcK ID

Not Available

Chemspider ID

56496

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62752

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1017211

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 Enol-3-Ethyl-1,2-cyclopentanedione (HMDB0031223)

MOL for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

3D MOL for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

3D SDF for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

3D-SDF for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

PDB for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

3D PDB for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

SMILES for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

INCHI for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

Structure for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

3D Structure for HMDB0031223 (Enol-3-Ethyl-1,2-cyclopentanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra