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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 01:10:55 UTC

Update Date

2023-02-21 17:27:03 UTC

HMDB ID

HMDB0039651

Secondary Accession Numbers

HMDB39651

Metabolite Identification

Common Name

3-Propyl-1,2-cyclopentanedione

Description

3-Propyl-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-Propyl-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-propyl-1,2-cyclopentanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Propyl-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-propyl	HMDB
2-Hydroxy-3-propyl-2-cyclopenten-1-one, 9ci	HMDB

Chemical Formula

C₈H₁₂O₂

Average Molecular Weight

140.1797

Monoisotopic Molecular Weight

140.083729628

IUPAC Name

3-propylcyclopentane-1,2-dione

Traditional Name

3-propylcyclopentane-1,2-dione

CAS Registry Number

25684-04-2

SMILES

CCCC1CCC(=O)C1=O

InChI Identifier

InChI=1S/C8H12O2/c1-2-3-6-4-5-7(9)8(6)10/h6H,2-5H2,1H3

InChI Key

QBJXYRWUKSOXQY-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

Membrane (HMDB: HMDB0039651)
Cell membrane (HMDB: HMDB0039651)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039651)

Source

Exogenous

Food

Food (HMDB: HMDB0039651)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0039651)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039651)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	56 - 57 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	962.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.07 g/L	ALOGPS
logP	1.57	ALOGPS
logP	2.32	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	16.16	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	2	ChemAxon
Refractivity	38.17 m³·mol⁻¹	ChemAxon
Polarizability	15.28 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]+	130.414	31661259
DarkChem	[M-H]-	126.338	31661259
DeepCCS	[M+H]+	133.529	30932474
DeepCCS	[M-H]-	130.505	30932474
DeepCCS	[M-2H]-	167.401	30932474
DeepCCS	[M+Na]+	142.337	30932474
AllCCS	[M+H]+	131.0	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	135.2	32859911
AllCCS	[M+Na]+	136.4	32859911
AllCCS	[M-H]-	132.3	32859911
AllCCS	[M+Na-2H]-	134.0	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Propyl-1,2-cyclopentanedione	CCCC1CCC(=O)C1=O	1843.8	Standard polar	33892256
3-Propyl-1,2-cyclopentanedione	CCCC1CCC(=O)C1=O	1163.2	Standard non polar	33892256
3-Propyl-1,2-cyclopentanedione	CCCC1CCC(=O)C1=O	1197.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Propyl-1,2-cyclopentanedione,1TMS,isomer #1	CCCC1=C(O[Si](C)(C)C)C(=O)CC1	1361.0	Semi standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TMS,isomer #1	CCCC1=C(O[Si](C)(C)C)C(=O)CC1	1297.6	Standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TMS,isomer #2	CCCC1CC=C(O[Si](C)(C)C)C1=O	1371.1	Semi standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TMS,isomer #2	CCCC1CC=C(O[Si](C)(C)C)C1=O	1296.7	Standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,2TMS,isomer #1	CCCC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1513.3	Semi standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,2TMS,isomer #1	CCCC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1582.9	Standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CCCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1	1589.3	Semi standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CCCC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1	1503.4	Standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CCCC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O	1584.9	Semi standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CCCC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O	1506.9	Standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CCCC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1967.8	Semi standard non polar	33892256
3-Propyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CCCC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1850.0	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-Propyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9200000000-66a3096f77c9f86b2bd2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Propyl-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-Propyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-0006-2900000000-809e5adf772a631aced4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-05mo-9300000000-96d9f8dc6af4700b23ae	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-0pbc-9000000000-4519e0fef8be18266556	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-000i-0900000000-456f3b8c4fbdc15c22d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-000i-2900000000-fdd61dbd8999f5893836	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-052g-9100000000-4b2b3f5705f70b333352	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-00dj-6900000000-8245107a78f69df5e09d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-01ox-9200000000-b202657390bd867cbd6d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-052f-9000000000-dd0ca8edaf4cfd4e71f0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-000i-0900000000-a5734f49b62679635a5a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-000i-2900000000-3077a4c9c3adec460b57	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Propyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-0006-9200000000-ee3ee576ea397330f28a	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

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

Membrane (predicted from logP)

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

FDB019280

KNApSAcK ID

Not Available

Chemspider ID

35014847

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54219268

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1619071

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-Propyl-1,2-cyclopentanedione (HMDB0039651)

MOL for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

3D MOL for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

3D SDF for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

3D-SDF for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

PDB for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

3D PDB for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

SMILES for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

INCHI for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

Structure for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

3D Structure for HMDB0039651 (3-Propyl-1,2-cyclopentanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra