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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:30 UTC

HMDB ID

HMDB0001184

Secondary Accession Numbers

HMDB01184

Metabolite Identification

Common Name

Methyl propenyl ketone

Description

Methyl propenyl ketone, also known as (3E)-3-penten-2-one or 2-oxo-3-pentene, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, methyl propenyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. Methyl propenyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Methyl propenyl ketone, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease and ulcerative colitis. Methyl propenyl ketone has also been linked to the inborn metabolic disorder celiac disease. Methyl propenyl ketone is occasionally found as a volatile component of normal human biofluids. It is found as a volatile in the hawthorn fruit upon ripening, and also is part of the scent components of the urine of some animals. Methyl propenyl ketone is a volatile organic compound.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3E)-Penten-2-one	ChEBI
(e)-3-Penten-2-one	ChEBI
(e)-Pent-3-en-2-one	ChEBI
trans-3-Penten-2-one	ChEBI
(3E)-3-Penten-2-one	HMDB
(3E)-Pent-3-en-2-one	HMDB
2-oxo-3-Pentene	HMDB
3-Penten-2-one	HMDB
3-Penten-2-one (methyl vinyl ketone)	HMDB
Ethylidene acetone	HMDB
FEMA no. 3417	HMDB
Methyl 1-propenyl ketone	HMDB
Pent-3-en-2-one	HMDB
2-oxo-(3E)-Pentene	ChEBI

Chemical Formula

C₅H₈O

Average Molecular Weight

84.1164

Monoisotopic Molecular Weight

84.057514878

IUPAC Name

(3E)-pent-3-en-2-one

Traditional Name

(E)-3-penten-2-one

CAS Registry Number

625-33-2

SMILES

C\C=C\C(C)=O

InChI Identifier

InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+

InChI Key

LABTWGUMFABVFG-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000028 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Source

Endogenous

Endogenous (HMDB: HMDB0001184)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	122.5 °C	Not Available
Water Solubility	46180 mg/l @ 25 °C (est)	The Good Scents Company Information System
LogP	0.52	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	32.2 g/L	ALOGPS
logP	1.48	ALOGPS
logP	1.25	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	19.86	ChemAxon
pKa (Strongest Basic)	-4.5	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	1	ChemAxon
Refractivity	26.52 m³·mol⁻¹	ChemAxon
Polarizability	9.65 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
AllCCS	[M+H]+	120.492	32859911
AllCCS	[M-H]-	127.089	32859911
DeepCCS	[M+H]+	126.087	30932474
DeepCCS	[M-H]-	124.191	30932474
DeepCCS	[M-2H]-	159.845	30932474
DeepCCS	[M+Na]+	134.332	30932474
AllCCS	[M+H]+	120.5	32859911
AllCCS	[M+H-H2O]+	115.9	32859911
AllCCS	[M+NH4]+	124.8	32859911
AllCCS	[M+Na]+	126.0	32859911
AllCCS	[M-H]-	127.1	32859911
AllCCS	[M+Na-2H]-	131.7	32859911
AllCCS	[M+HCOO]-	136.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl propenyl ketone	C\C=C\C(C)=O	1074.3	Standard polar	33892256
Methyl propenyl ketone	C\C=C\C(C)=O	694.0	Standard non polar	33892256
Methyl propenyl ketone	C\C=C\C(C)=O	731.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl propenyl ketone,1TMS,isomer #1	C=C(/C=C/C)O[Si](C)(C)C	909.0	Semi standard non polar	33892256
Methyl propenyl ketone,1TMS,isomer #1	C=C(/C=C/C)O[Si](C)(C)C	893.7	Standard non polar	33892256
Methyl propenyl ketone,1TMS,isomer #1	C=C(/C=C/C)O[Si](C)(C)C	1025.2	Standard polar	33892256
Methyl propenyl ketone,1TBDMS,isomer #1	C=C(/C=C/C)O[Si](C)(C)C(C)(C)C	1135.3	Semi standard non polar	33892256
Methyl propenyl ketone,1TBDMS,isomer #1	C=C(/C=C/C)O[Si](C)(C)C(C)(C)C	1129.6	Standard non polar	33892256
Methyl propenyl ketone,1TBDMS,isomer #1	C=C(/C=C/C)O[Si](C)(C)C(C)(C)C	1224.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl propenyl ketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-2a109e7c365cab33928d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl propenyl ketone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9000000000-9846367d6d2a4fccf15a	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl propenyl ketone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0159-9000000000-bc23095f98a3d62d8edd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl propenyl ketone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-39b3225b4599f0b9fece	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl propenyl ketone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-ad93b895a094f9746ea9	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 10V, Positive-QTOF	splash10-00kr-9000000000-ac38750221ab3bdad6b8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 20V, Positive-QTOF	splash10-014r-9000000000-4ae15cb28a34c2a1f00e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 40V, Positive-QTOF	splash10-00ko-9000000000-56e5e98dce43d5da8964	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 10V, Negative-QTOF	splash10-001i-9000000000-cb5d0885aced41920a6e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 20V, Negative-QTOF	splash10-001i-9000000000-d8de7d4bc075e7396c75	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 40V, Negative-QTOF	splash10-014l-9000000000-21ae70c7017fc0567b86	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 10V, Negative-QTOF	splash10-001i-9000000000-1fe8bbf8f6ab17ae0b2b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 20V, Negative-QTOF	splash10-00lr-9000000000-811992e68b697e85c4d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 40V, Negative-QTOF	splash10-014j-9000000000-906f526b3fa28ebed8bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 10V, Positive-QTOF	splash10-00kf-9000000000-1b83bf539bd4b5d8eeb2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 20V, Positive-QTOF	splash10-0006-9000000000-e9939d37400a5aaa0cd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl propenyl ketone 40V, Positive-QTOF	splash10-0006-9000000000-a8d38949c700c5246882	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	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, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	2012-12-05	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

Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112172

KNApSAcK ID

Not Available

Chemspider ID

553493

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637920

PDB ID

Not Available

ChEBI ID

145276

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1123851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [PubMed:914932 ]
Chen L, Xie B, Yu T: [Identification of volatile compounds of hawthorn by gas chromatography/mass spectrometry (GC/MS)]. Se Pu. 1997 May;15(3):219-21. [PubMed:15739361 ]
Rock F, Mueller S, Weimar U, Rammensee HG, Overath P: Comparative analysis of volatile constituents from mice and their urine. J Chem Ecol. 2006 Jun;32(6):1333-46. Epub 2006 May 31. [PubMed:16770722 ]

Showing metabocard for Methyl propenyl ketone (HMDB0001184)

MOL for HMDB0001184 (Methyl propenyl ketone)

3D MOL for HMDB0001184 (Methyl propenyl ketone)

3D SDF for HMDB0001184 (Methyl propenyl ketone)

3D-SDF for HMDB0001184 (Methyl propenyl ketone)

PDB for HMDB0001184 (Methyl propenyl ketone)

3D PDB for HMDB0001184 (Methyl propenyl ketone)

SMILES for HMDB0001184 (Methyl propenyl ketone)

INCHI for HMDB0001184 (Methyl propenyl ketone)

Structure for HMDB0001184 (Methyl propenyl ketone)

3D Structure for HMDB0001184 (Methyl propenyl ketone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra