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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 17:44:19 UTC

Update Date

2023-02-21 17:20:58 UTC

HMDB ID

HMDB0031606

Secondary Accession Numbers

HMDB31606

Metabolite Identification

Common Name

4-Penten-2-one

Description

4-Penten-2-one belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 4-penten-2-one is considered to be an oxygenated hydrocarbon. 4-Penten-2-one has been detected, but not quantified in, fruits and tamarinds (Tamarindus indica). This could make 4-penten-2-one a potential biomarker for the consumption of these foods. 4-Penten-2-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4-Penten-2-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
Allyl methyl ketone	HMDB
Vinylacetone	HMDB

Chemical Formula

C₅H₈O

Average Molecular Weight

84.1164

Monoisotopic Molecular Weight

84.057514878

IUPAC Name

pent-4-en-2-one

Traditional Name

pent-4-en-2-one

CAS Registry Number

13891-87-7

SMILES

CC(=O)CC=C

InChI Identifier

InChI=1S/C5H8O/c1-3-4-5(2)6/h3H,1,4H2,2H3

InChI Key

PNJWIWWMYCMZRO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl ketone (CHEBI:87508 )
olefinic compound (CHEBI:87508 )
Oxygenated hydrocarbons (LMFA12000034 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031606)
Cytoplasm (HMDB: HMDB0031606)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031606)

Source

Endogenous

Endogenous (HMDB: HMDB0031606)

Plant

Plant (HMDB: HMDB0031606)

Exogenous

Food

Food (HMDB: HMDB0031606)

Fruit

Tropical fruit

Tamarind (FooDB: FOOD00180)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	93.00 to 94.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	38630 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.734 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.6 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.95	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	16.89	ChemAxon
pKa (Strongest Basic)	-7.4	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	2	ChemAxon
Refractivity	25.47 m³·mol⁻¹	ChemAxon
Polarizability	9.49 Å³	ChemAxon
Number of Rings	0	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]+	116.402	31661259
DarkChem	[M-H]-	110.15	31661259
DeepCCS	[M+H]+	122.641	30932474
DeepCCS	[M-H]-	120.639	30932474
DeepCCS	[M-2H]-	156.081	30932474
DeepCCS	[M+Na]+	130.612	30932474
AllCCS	[M+H]+	121.1	32859911
AllCCS	[M+H-H2O]+	116.6	32859911
AllCCS	[M+NH4]+	125.4	32859911
AllCCS	[M+Na]+	126.6	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	136.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Penten-2-one	CC(=O)CC=C	1000.7	Standard polar	33892256
4-Penten-2-one	CC(=O)CC=C	654.1	Standard non polar	33892256
4-Penten-2-one	CC(=O)CC=C	662.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Penten-2-one,1TMS,isomer #1	C=CC=C(C)O[Si](C)(C)C	937.0	Semi standard non polar	33892256
4-Penten-2-one,1TMS,isomer #1	C=CC=C(C)O[Si](C)(C)C	871.1	Standard non polar	33892256
4-Penten-2-one,1TMS,isomer #2	C=CCC(=C)O[Si](C)(C)C	846.0	Semi standard non polar	33892256
4-Penten-2-one,1TMS,isomer #2	C=CCC(=C)O[Si](C)(C)C	877.7	Standard non polar	33892256
4-Penten-2-one,1TBDMS,isomer #1	C=CC=C(C)O[Si](C)(C)C(C)(C)C	1154.7	Semi standard non polar	33892256
4-Penten-2-one,1TBDMS,isomer #1	C=CC=C(C)O[Si](C)(C)C(C)(C)C	1083.9	Standard non polar	33892256
4-Penten-2-one,1TBDMS,isomer #2	C=CCC(=C)O[Si](C)(C)C(C)(C)C	1072.4	Semi standard non polar	33892256
4-Penten-2-one,1TBDMS,isomer #2	C=CCC(=C)O[Si](C)(C)C(C)(C)C	1087.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Penten-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-e3643da738262b7934b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Penten-2-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 - 4-Penten-2-one 10V, Positive-QTOF	splash10-00kr-9000000000-d86bae5f84fb12f75935	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 20V, Positive-QTOF	splash10-014r-9000000000-f3227d3a1f1754439dee	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 40V, Positive-QTOF	splash10-0fr6-9000000000-fd945e5cbec3db71add7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 10V, Negative-QTOF	splash10-001i-9000000000-97b749961df8c9f3ff3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 20V, Negative-QTOF	splash10-001i-9000000000-ce4bceb29f3a5e9fcfb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 40V, Negative-QTOF	splash10-014l-9000000000-bd76a1036f06e0c9b9b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 10V, Negative-QTOF	splash10-001i-9000000000-1fe8bbf8f6ab17ae0b2b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 20V, Negative-QTOF	splash10-0a59-9000000000-fddfc35b562a5d2be643	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 40V, Negative-QTOF	splash10-0a4m-9000000000-b08432ddc7924168882a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 10V, Positive-QTOF	splash10-0006-9000000000-348890c11e795a93b918	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 20V, Positive-QTOF	splash10-0006-9000000000-e3adde02fb3cf5a5af22	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Penten-2-one 40V, Positive-QTOF	splash10-0006-9000000000-fcf1d4fe2f86c7f23892	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB008242

KNApSAcK ID

C00054486

Chemspider ID

75618

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83797

PDB ID

Not Available

ChEBI ID

87508

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1458821

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 4-Penten-2-one (HMDB0031606)

MOL for HMDB0031606 (4-Penten-2-one)

3D MOL for HMDB0031606 (4-Penten-2-one)

3D SDF for HMDB0031606 (4-Penten-2-one)

3D-SDF for HMDB0031606 (4-Penten-2-one)

PDB for HMDB0031606 (4-Penten-2-one)

3D PDB for HMDB0031606 (4-Penten-2-one)

SMILES for HMDB0031606 (4-Penten-2-one)

INCHI for HMDB0031606 (4-Penten-2-one)

Structure for HMDB0031606 (4-Penten-2-one)

3D Structure for HMDB0031606 (4-Penten-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra