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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

HMDB0031550

Secondary Accession Numbers

HMDB31550

Metabolite Identification

Common Name

5-Methyl-3-hexen-2-one

Description

5-Methyl-3-hexen-2-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. 5-Methyl-3-hexen-2-one is a sweet, berry, and cheese tasting compound. Based on a literature review very few articles have been published on 5-Methyl-3-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
(3E)-5-Methyl-3-hexen-2-one	HMDB
3-Hexen-2-one, 5-me	HMDB
5-Methyl-hex-3-en-2-one	HMDB
FEMA 3409	HMDB
Isobutylideneacetone	HMDB

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.1696

Monoisotopic Molecular Weight

112.088815006

IUPAC Name

(3Z)-5-methylhex-3-en-2-one

Traditional Name

(3Z)-5-methylhex-3-en-2-one

CAS Registry Number

5166-53-0

SMILES

CC(C)\C=C/C(C)=O

InChI Identifier

InChI=1S/C7H12O/c1-6(2)4-5-7(3)8/h4-6H,1-3H3/b5-4-

InChI Key

IYMKNYVCXUEFJE-PLNGDYQASA-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

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031550)
Cytoplasm (HMDB: HMDB0031550)

Source

Exogenous

Food

Food (HMDB: HMDB0031550)

Exogenous (HMDB: HMDB0031550)

Endogenous

Endogenous (HMDB: HMDB0031550)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031550)

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	2.09 g/L	ALOGPS
logP	1.56	ALOGPS
logP	1.98	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	-4.6	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	35.67 m³·mol⁻¹	ChemAxon
Polarizability	13.4 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
DeepCCS	[M+H]+	131.453	30932474
DeepCCS	[M-H]-	129.062	30932474
DeepCCS	[M-2H]-	165.381	30932474
DeepCCS	[M+Na]+	140.198	30932474
AllCCS	[M+H]+	125.4	32859911
AllCCS	[M+H-H2O]+	121.0	32859911
AllCCS	[M+NH4]+	129.5	32859911
AllCCS	[M+Na]+	130.6	32859911
AllCCS	[M-H]-	128.8	32859911
AllCCS	[M+Na-2H]-	132.0	32859911
AllCCS	[M+HCOO]-	135.7	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.	4.13 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1504 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1816.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	511.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	330.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	519.7 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	540.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1100.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.7 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	1211.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	429.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	455.0 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	59.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-3-hexen-2-one	CC(C)\C=C/C(C)=O	1288.5	Standard polar	33892256
5-Methyl-3-hexen-2-one	CC(C)\C=C/C(C)=O	853.5	Standard non polar	33892256
5-Methyl-3-hexen-2-one	CC(C)\C=C/C(C)=O	883.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-3-hexen-2-one,1TMS,isomer #1	C=C(/C=C\C(C)C)O[Si](C)(C)C	1038.0	Semi standard non polar	33892256
5-Methyl-3-hexen-2-one,1TMS,isomer #1	C=C(/C=C\C(C)C)O[Si](C)(C)C	1047.7	Standard non polar	33892256
5-Methyl-3-hexen-2-one,1TBDMS,isomer #1	C=C(/C=C\C(C)C)O[Si](C)(C)C(C)(C)C	1272.5	Semi standard non polar	33892256
5-Methyl-3-hexen-2-one,1TBDMS,isomer #1	C=C(/C=C\C(C)C)O[Si](C)(C)C(C)(C)C	1275.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-3-hexen-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mp-9000000000-06c0c575a9e079d80dfd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-3-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-3-hexen-2-one 10V, Positive-QTOF	splash10-03dj-9700000000-a03505da850ac54aa89b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 20V, Positive-QTOF	splash10-01ot-9400000000-e96255c49f30a86af0db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 40V, Positive-QTOF	splash10-0uxv-9000000000-75052411fcf64a96ff1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 10V, Negative-QTOF	splash10-03di-2900000000-cb7b48ed63fb26bc5935	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 20V, Negative-QTOF	splash10-03di-6900000000-372fd9f9f359b0028fa5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 40V, Negative-QTOF	splash10-00kg-9000000000-0f46553d1ca52555bbd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 10V, Negative-QTOF	splash10-03di-3900000000-3ab11b2a9c227aad983e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 20V, Negative-QTOF	splash10-03dl-6900000000-a6dd48478624a771c226	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 40V, Negative-QTOF	splash10-002f-9000000000-4410ae0c16ca4b96dbf1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 10V, Positive-QTOF	splash10-054n-9000000000-82b78a44283fb73718b7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 20V, Positive-QTOF	splash10-0zi3-9000000000-24238c98016755c4c883	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-3-hexen-2-one 40V, Positive-QTOF	splash10-0006-9000000000-a996c3415f3208317c96	2021-09-24	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

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

FDB008161

KNApSAcK ID

Not Available

Chemspider ID

30776907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

27796011

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-3-hexen-2-one (HMDB0031550)

MOL for HMDB0031550 (5-Methyl-3-hexen-2-one)

3D MOL for HMDB0031550 (5-Methyl-3-hexen-2-one)

3D SDF for HMDB0031550 (5-Methyl-3-hexen-2-one)

3D-SDF for HMDB0031550 (5-Methyl-3-hexen-2-one)

PDB for HMDB0031550 (5-Methyl-3-hexen-2-one)

3D PDB for HMDB0031550 (5-Methyl-3-hexen-2-one)

SMILES for HMDB0031550 (5-Methyl-3-hexen-2-one)

INCHI for HMDB0031550 (5-Methyl-3-hexen-2-one)

Structure for HMDB0031550 (5-Methyl-3-hexen-2-one)

3D Structure for HMDB0031550 (5-Methyl-3-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