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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:04 UTC

Update Date

2023-02-21 17:20:50 UTC

HMDB ID

HMDB0031564

Secondary Accession Numbers

HMDB31564

Metabolite Identification

Common Name

4-Methyl-4-penten-2-one

Description

4-Methyl-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. 4-Methyl-4-penten-2-one is an acrylic, pungent, and vegetable tasting compound. Based on a literature review very few articles have been published on 4-Methyl-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
3-Acetylisobutene	HMDB
Isopropenylacetone	HMDB

Chemical Formula

C₆H₁₀O

Average Molecular Weight

98.143

Monoisotopic Molecular Weight

98.073164942

IUPAC Name

4-methylpent-4-en-2-one

Traditional Name

isomesityl oxide

CAS Registry Number

3744-02-3

SMILES

CC(=C)CC(C)=O

InChI Identifier

InChI=1S/C6H10O/c1-5(2)4-6(3)7/h1,4H2,2-3H3

InChI Key

VADUDTKCGJKNDY-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

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Pungent

Odor

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0031564)

Exogenous

Food

Food (HMDB: HMDB0031564)

Exogenous (HMDB: HMDB0031564)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031564)

Role

Biological role

Energy source (HMDB: HMDB0031564)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031564)

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	16.8 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.19	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	17.21	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	29.75 m³·mol⁻¹	ChemAxon
Polarizability	11.28 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]+	121.689	31661259
DarkChem	[M-H]-	114.447	31661259
DeepCCS	[M+H]+	126.329	30932474
DeepCCS	[M-H]-	124.419	30932474
DeepCCS	[M-2H]-	160.167	30932474
DeepCCS	[M+Na]+	134.723	30932474
AllCCS	[M+H]+	123.2	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	127.3	32859911
AllCCS	[M+Na]+	128.5	32859911
AllCCS	[M-H]-	125.4	32859911
AllCCS	[M+Na-2H]-	129.3	32859911
AllCCS	[M+HCOO]-	133.6	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. Predicted by Afia on May 17, 2022.	3.64 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4655 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.34 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1683.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	468.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	299.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	402.1 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	527.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	969.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	338.5 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	1062.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	421.0 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	57.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-4-penten-2-one	CC(=C)CC(C)=O	1035.6	Standard polar	33892256
4-Methyl-4-penten-2-one	CC(=C)CC(C)=O	750.9	Standard non polar	33892256
4-Methyl-4-penten-2-one	CC(=C)CC(C)=O	725.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-4-penten-2-one,1TMS,isomer #1	C=C(C)C=C(C)O[Si](C)(C)C	970.3	Semi standard non polar	33892256
4-Methyl-4-penten-2-one,1TMS,isomer #1	C=C(C)C=C(C)O[Si](C)(C)C	955.0	Standard non polar	33892256
4-Methyl-4-penten-2-one,1TMS,isomer #2	C=C(C)CC(=C)O[Si](C)(C)C	929.9	Semi standard non polar	33892256
4-Methyl-4-penten-2-one,1TMS,isomer #2	C=C(C)CC(=C)O[Si](C)(C)C	947.8	Standard non polar	33892256
4-Methyl-4-penten-2-one,1TBDMS,isomer #1	C=C(C)C=C(C)O[Si](C)(C)C(C)(C)C	1181.6	Semi standard non polar	33892256
4-Methyl-4-penten-2-one,1TBDMS,isomer #1	C=C(C)C=C(C)O[Si](C)(C)C(C)(C)C	1165.8	Standard non polar	33892256
4-Methyl-4-penten-2-one,1TBDMS,isomer #2	C=C(C)CC(=C)O[Si](C)(C)C(C)(C)C	1127.8	Semi standard non polar	33892256
4-Methyl-4-penten-2-one,1TBDMS,isomer #2	C=C(C)CC(=C)O[Si](C)(C)C(C)(C)C	1139.6	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-Methyl-4-penten-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-8640d99f89487e8c0959	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-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-Methyl-4-penten-2-one 10V, Positive-QTOF	splash10-000t-9000000000-a486d3e4e580c3a5f6aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 20V, Positive-QTOF	splash10-001j-9000000000-a0c652af39c3fd33817a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 40V, Positive-QTOF	splash10-000x-9000000000-27d924150625b45252ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 10V, Negative-QTOF	splash10-0002-9000000000-f5017bcd7ba3ffb3ba7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 20V, Negative-QTOF	splash10-0002-9000000000-46acc0b8accd8659ab53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 40V, Negative-QTOF	splash10-0560-9000000000-6501736baad6aada43b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 10V, Positive-QTOF	splash10-000x-9000000000-55029415f0dbf68d9eac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 20V, Positive-QTOF	splash10-0536-9000000000-a76314591203ac5ab2c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 40V, Positive-QTOF	splash10-000l-9000000000-34d70dd0550618abde2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 10V, Negative-QTOF	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 20V, Negative-QTOF	splash10-0002-9000000000-ec0ca1ae03c7514c0f52	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-penten-2-one 40V, Negative-QTOF	splash10-0a4i-9000000000-53dd22ec21c41dda821f	2021-09-22	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]+)	2023-02-04	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
Membrane

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

FDB008179

KNApSAcK ID

C00050956

Chemspider ID

23350988

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19543

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 4-Methyl-4-penten-2-one (HMDB0031564)

MOL for HMDB0031564 (4-Methyl-4-penten-2-one)

3D MOL for HMDB0031564 (4-Methyl-4-penten-2-one)

3D SDF for HMDB0031564 (4-Methyl-4-penten-2-one)

3D-SDF for HMDB0031564 (4-Methyl-4-penten-2-one)

PDB for HMDB0031564 (4-Methyl-4-penten-2-one)

3D PDB for HMDB0031564 (4-Methyl-4-penten-2-one)

SMILES for HMDB0031564 (4-Methyl-4-penten-2-one)

INCHI for HMDB0031564 (4-Methyl-4-penten-2-one)

Structure for HMDB0031564 (4-Methyl-4-penten-2-one)

3D Structure for HMDB0031564 (4-Methyl-4-penten-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra