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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:00 UTC

Update Date

2023-02-21 17:20:48 UTC

HMDB ID

HMDB0031551

Secondary Accession Numbers

HMDB31551

Metabolite Identification

Common Name

5-Methyl-5-hexen-2-one

Description

5-Methyl-5-hexen-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. 5-Methyl-5-hexen-2-one is a foliage, green, and vegetable tasting compound. Based on a literature review very few articles have been published on 5-Methyl-5-hexen-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
4-Acetyl-2-methyl-1-butene	HMDB
FEMA 3365	HMDB
Methallylacetone	HMDB

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.1696

Monoisotopic Molecular Weight

112.088815006

IUPAC Name

5-methylhex-5-en-2-one

Traditional Name

5-hexen-2-one, 5-methyl-

CAS Registry Number

3240-09-3

SMILES

CC(=C)CCC(C)=O

InChI Identifier

InChI=1S/C7H12O/c1-6(2)4-5-7(3)8/h1,4-5H2,2-3H3

InChI Key

VBCIOOKAKHGVMI-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

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0031551)

Exogenous

Food

Food (HMDB: HMDB0031551)

Exogenous (HMDB: HMDB0031551)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031551)

Role

Biological role

Energy source (HMDB: HMDB0031551)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031551)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031551)

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	7.53 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.64	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	19.6	ChemAxon
pKa (Strongest Basic)	-7.3	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	3	ChemAxon
Refractivity	34.35 m³·mol⁻¹	ChemAxon
Polarizability	13.32 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]+	125.856	31661259
DarkChem	[M-H]-	120.448	31661259
DeepCCS	[M+H]+	128.229	30932474
DeepCCS	[M-H]-	126.159	30932474
DeepCCS	[M-2H]-	161.898	30932474
DeepCCS	[M+Na]+	136.623	30932474
AllCCS	[M+H]+	126.4	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	130.4	32859911
AllCCS	[M+Na]+	131.6	32859911
AllCCS	[M-H]-	127.9	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	134.8	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.	3.99 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9267 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1854.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	506.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	329.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	158.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.6 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	602.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1112.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	379.4 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	1194.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	448.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	447.8 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	35.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-5-hexen-2-one	CC(=C)CCC(C)=O	1268.7	Standard polar	33892256
5-Methyl-5-hexen-2-one	CC(=C)CCC(C)=O	856.7	Standard non polar	33892256
5-Methyl-5-hexen-2-one	CC(=C)CCC(C)=O	849.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-5-hexen-2-one,1TMS,isomer #1	C=C(C)CC=C(C)O[Si](C)(C)C	1073.6	Semi standard non polar	33892256
5-Methyl-5-hexen-2-one,1TMS,isomer #1	C=C(C)CC=C(C)O[Si](C)(C)C	1010.6	Standard non polar	33892256
5-Methyl-5-hexen-2-one,1TMS,isomer #2	C=C(C)CCC(=C)O[Si](C)(C)C	1013.2	Semi standard non polar	33892256
5-Methyl-5-hexen-2-one,1TMS,isomer #2	C=C(C)CCC(=C)O[Si](C)(C)C	1044.8	Standard non polar	33892256
5-Methyl-5-hexen-2-one,1TBDMS,isomer #1	C=C(C)CC=C(C)O[Si](C)(C)C(C)(C)C	1275.7	Semi standard non polar	33892256
5-Methyl-5-hexen-2-one,1TBDMS,isomer #1	C=C(C)CC=C(C)O[Si](C)(C)C(C)(C)C	1242.3	Standard non polar	33892256
5-Methyl-5-hexen-2-one,1TBDMS,isomer #2	C=C(C)CCC(=C)O[Si](C)(C)C(C)(C)C	1216.9	Semi standard non polar	33892256
5-Methyl-5-hexen-2-one,1TBDMS,isomer #2	C=C(C)CCC(=C)O[Si](C)(C)C(C)(C)C	1245.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-5-hexen-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-8c83d2c0592f4e3b6179	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-5-hexen-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-5-hexen-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 - 5-Methyl-5-hexen-2-one 10V, Positive-QTOF	splash10-03dj-9700000000-9b0bc608a92c67d390af	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 20V, Positive-QTOF	splash10-01ot-9300000000-0c9004fccd0c465d7e11	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 40V, Positive-QTOF	splash10-0fvj-9000000000-e938e1ea0ea387d5ffb2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 10V, Negative-QTOF	splash10-03di-1900000000-53eb8ac1db785070dd62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 20V, Negative-QTOF	splash10-03di-3900000000-45d6973d983c56518ed6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 40V, Negative-QTOF	splash10-0005-9000000000-1dfa32a3759b14f0bc86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 10V, Negative-QTOF	splash10-03di-0900000000-6e2ef191e20e94bd344c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 20V, Negative-QTOF	splash10-03dl-9700000000-8769f7bf17ec3fbb0153	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 40V, Negative-QTOF	splash10-002g-9000000000-a57bb5f213eefb27cf5e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 10V, Positive-QTOF	splash10-0a4j-9000000000-f83e96accaecd65573d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 20V, Positive-QTOF	splash10-014i-9000000000-2bdb57ee3ea45a0259f0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-5-hexen-2-one 40V, Positive-QTOF	splash10-0173-9000000000-de89000fd20e0e9b31aa	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	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

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

FDB008163

KNApSAcK ID

Not Available

Chemspider ID

198976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

228604

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 5-Methyl-5-hexen-2-one (HMDB0031551)

MOL for HMDB0031551 (5-Methyl-5-hexen-2-one)

3D MOL for HMDB0031551 (5-Methyl-5-hexen-2-one)

3D SDF for HMDB0031551 (5-Methyl-5-hexen-2-one)

3D-SDF for HMDB0031551 (5-Methyl-5-hexen-2-one)

PDB for HMDB0031551 (5-Methyl-5-hexen-2-one)

3D PDB for HMDB0031551 (5-Methyl-5-hexen-2-one)

SMILES for HMDB0031551 (5-Methyl-5-hexen-2-one)

INCHI for HMDB0031551 (5-Methyl-5-hexen-2-one)

Structure for HMDB0031551 (5-Methyl-5-hexen-2-one)

3D Structure for HMDB0031551 (5-Methyl-5-hexen-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