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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:44:11 UTC

Update Date

2023-02-21 17:20:54 UTC

HMDB ID

HMDB0031582

Secondary Accession Numbers

HMDB31582

Metabolite Identification

Common Name

6-Methyl-3,5-heptadien-2-one

Description

6-Methyl-3,5-heptadien-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'. 6-Methyl-3,5-heptadien-2-one is a sweet, cinnamon, and coconut tasting compound. 6-Methyl-3,5-heptadien-2-one has been detected, but not quantified in, a few different foods, such as cherry tomatoes (Solanum lycopersicum var. cerasiforme), garden tomatoes (Solanum lycopersicum), and garden tomato (var.). This could make 6-methyl-3,5-heptadien-2-one a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 6-Methyl-3,5-heptadien-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)-6-Methyl-3,5-heptadien-2-one	HMDB
2-Methyl-2,4-heptadien-6-one	HMDB
2-Methylhepta-2,4-dien-6-one	HMDB
6-Methyl-(e)-3,5-heptadien-2-one	HMDB
6-Methyl-3,5-heptadiene-2-one	HMDB
6-Methyl-3,5-heptadienone-2	HMDB
6-Methyl-hepta-3,5-diene-2-one	HMDB
6-Methylhepta-3,5-dien-2-one	HMDB
FEMA 3363	HMDB
Methylheptadienone	HMDB

Chemical Formula

C₈H₁₂O

Average Molecular Weight

124.1803

Monoisotopic Molecular Weight

124.088815006

IUPAC Name

(3Z)-6-methylhepta-3,5-dien-2-one

Traditional Name

(3Z)-6-methylhepta-3,5-dien-2-one

CAS Registry Number

1604-28-0

SMILES

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

InChI Identifier

InChI=1S/C8H12O/c1-7(2)5-4-6-8(3)9/h4-6H,1-3H3/b6-4-

InChI Key

KSKXSFZGARKWOW-XQRVVYSFSA-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

Sweet

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031582)
Cytoplasm (HMDB: HMDB0031582)

Source

Endogenous

Endogenous (HMDB: HMDB0031582)

Exogenous

Food

Food (HMDB: HMDB0031582)

Vegetable

Fruit vegetable

Exogenous (HMDB: HMDB0031582)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031582)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	190.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.679 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2.02	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	19.73	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	2	ChemAxon
Refractivity	41.12 m³·mol⁻¹	ChemAxon
Polarizability	14.82 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]+	132.572	30932474
DeepCCS	[M-H]-	129.896	30932474
DeepCCS	[M-2H]-	166.437	30932474
DeepCCS	[M+Na]+	141.464	30932474
AllCCS	[M+H]+	127.3	32859911
AllCCS	[M+H-H2O]+	122.9	32859911
AllCCS	[M+NH4]+	131.3	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	130.7	32859911
AllCCS	[M+HCOO]-	133.7	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.	5.44 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9135 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1964.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	483.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	317.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	102.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	472.1 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	469.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1141.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	440.8 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	1060.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	368.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.9 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	50.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methyl-3,5-heptadien-2-one	CC(C)=C\C=C/C(C)=O	1513.1	Standard polar	33892256
6-Methyl-3,5-heptadien-2-one	CC(C)=C\C=C/C(C)=O	1045.6	Standard non polar	33892256
6-Methyl-3,5-heptadien-2-one	CC(C)=C\C=C/C(C)=O	1094.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Methyl-3,5-heptadien-2-one,1TMS,isomer #1	C=C(/C=C\C=C(C)C)O[Si](C)(C)C	1241.0	Semi standard non polar	33892256
6-Methyl-3,5-heptadien-2-one,1TMS,isomer #1	C=C(/C=C\C=C(C)C)O[Si](C)(C)C	1192.7	Standard non polar	33892256
6-Methyl-3,5-heptadien-2-one,1TBDMS,isomer #1	C=C(/C=C\C=C(C)C)O[Si](C)(C)C(C)(C)C	1450.2	Semi standard non polar	33892256
6-Methyl-3,5-heptadien-2-one,1TBDMS,isomer #1	C=C(/C=C\C=C(C)C)O[Si](C)(C)C(C)(C)C	1413.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methyl-3,5-heptadien-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-9300000000-c94710d8500612cf2b83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methyl-3,5-heptadien-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methyl-3,5-heptadien-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 - 6-Methyl-3,5-heptadien-2-one 10V, Positive-QTOF	splash10-056r-1900000000-0e9f02948079b76c8690	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 20V, Positive-QTOF	splash10-0ar0-9800000000-6abec9975a531a09f7e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 40V, Positive-QTOF	splash10-0ldi-9000000000-b9fb9241a09f70031806	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 10V, Negative-QTOF	splash10-00di-0900000000-2b948eeb56dd05a01279	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 20V, Negative-QTOF	splash10-00di-3900000000-37e17326ab5207d08de4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 40V, Negative-QTOF	splash10-0a4i-9600000000-aca6495ab2f4090aa841	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 10V, Positive-QTOF	splash10-05o3-9100000000-d16f5bef50f96ab0007f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 20V, Positive-QTOF	splash10-05mo-9100000000-62b5d32becb128f96788	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 40V, Positive-QTOF	splash10-0006-9000000000-bf187afca89861bbe62c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 10V, Negative-QTOF	splash10-00di-1900000000-4f62cb65ad05955b218b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 20V, Negative-QTOF	splash10-0a4i-3900000000-8c9b890ac12e1691dda7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methyl-3,5-heptadien-2-one 40V, Negative-QTOF	splash10-05n0-9000000000-cba90a2c48ba4bcff92b	2021-09-22	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

Feces

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	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	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 ]
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

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008208

KNApSAcK ID

Not Available

Chemspider ID

10435776

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12510894

PDB ID

Not Available

ChEBI ID

89984

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004501

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 6-Methyl-3,5-heptadien-2-one (HMDB0031582)

MOL for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

3D MOL for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

3D SDF for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

3D-SDF for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

PDB for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

3D PDB for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

SMILES for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

INCHI for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

Structure for HMDB0031582 (6-Methyl-3,5-heptadien-2-one)

3D Structure for HMDB0031582 (6-Methyl-3,5-heptadien-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