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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 20:57:49 UTC

Update Date

2023-02-21 17:24:57 UTC

HMDB ID

HMDB0035915

Secondary Accession Numbers

HMDB35915

Metabolite Identification

Common Name

Sulcatone

Description

Sulcatone, also known as methylheptenone or fema 2707, 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. Sulcatone is a very hydrophobic methylketone, practically insoluble in water, and relatively neutral. It exists as a clear, colorless liquid. Sulcatone can be found in all eukaryotes, ranging from yeast to plants to humans. Sulcatone has a musty, apple green-bean, and pear-like taste. and a citrus-like lemongrass odor. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil. Sulcatone is naturally found in bay leaf, blackberry fruit, sour cherries, cloves, ginger and lavender. In insects and animals, it has a role as an alarm or attractant pheromone. In fact, sulcatone is one of a number of mosquito attractants, especially for those species such as Aedes aegypti with the odor receptor gene Or4 (PMID:25391959 ). Sulcatone is secreted by humans in their sweat and is a compound frequently found in human body odors (but in few other mammals). Sulcoatone is used as a pheromone by ferrets, european badgers, red foxes, treefrogs, bedbugs, wasps and butterflies. Sulcatone is one of several ketones found in Cannabis sativa (PMID:6991645 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Methyl-5-hepten-2-one	ChEBI
6-Methylhept-5-en-2-one	ChEBI
Methylheptenone	Kegg
2-Methyl-2-hepten-6-one	HMDB
2-Methyl-6-heptenone	HMDB
2-Methyl-6-oxo-2-heptene	HMDB
2-Methylhept-2-en-6-one	HMDB
2-oxo-6-Methylhept-5-ene	HMDB
6-Methyl hept-5-en-2-one	HMDB
6-Methyl-5-heptene-2-one	HMDB
6-Methylheptan-5-ene-2-one	HMDB
FEMA 2707	HMDB
Prenylacetone	HMDB
6-Methylhept-5-ene-2-one	HMDB
Sulcatone	MeSH

Chemical Formula

C₈H₁₄O

Average Molecular Weight

126.1962

Monoisotopic Molecular Weight

126.10446507

IUPAC Name

6-methylhept-5-en-2-one

Traditional Name

6-methyl-5-hepten-2-one

CAS Registry Number

110-93-0

SMILES

CC(C)=CCCC(C)=O

InChI Identifier

InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3

InChI Key

UHEPJGULSIKKTP-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

methyl ketone (CHEBI:16310 )
heptenone (CHEBI:16310 )
Oxygenated hydrocarbons (LMFA12000039 )
an apocarotenoid (CPD-7969 )
a ketone (CPD-7969 )

Ontology

Ginger (FooDB: FOOD00206)
Cardamom (FooDB: FOOD00074)

Herb

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-67 °C	Not Available
Boiling Point	72.00 to 73.00 °C. @ 18.00 mm Hg	The Good Scents Company Information System
Water Solubility	3351 /mg/L @ 20 °C (exp)	The Good Scents Company Information System
LogP	1.947 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.54 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2.02	ChemAxon
logS	-1.6	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	40.02 m³·mol⁻¹	ChemAxon
Polarizability	15.53 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]+	130.056	31661259
DarkChem	[M-H]-	124.975	31661259
DeepCCS	[M+H]+	131.9	30932474
DeepCCS	[M-H]-	129.706	30932474
DeepCCS	[M-2H]-	165.811	30932474
DeepCCS	[M+Na]+	140.631	30932474
AllCCS	[M+H]+	129.1	32859911
AllCCS	[M+H-H2O]+	124.8	32859911
AllCCS	[M+NH4]+	133.1	32859911
AllCCS	[M+Na]+	134.2	32859911
AllCCS	[M-H]-	130.6	32859911
AllCCS	[M+Na-2H]-	133.4	32859911
AllCCS	[M+HCOO]-	136.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulcatone	CC(C)=CCCC(C)=O	1308.9	Standard polar	33892256
Sulcatone	CC(C)=CCCC(C)=O	959.3	Standard non polar	33892256
Sulcatone	CC(C)=CCCC(C)=O	974.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulcatone,1TMS,isomer #1	CC(C)=CCC=C(C)O[Si](C)(C)C	1184.4	Semi standard non polar	33892256
Sulcatone,1TMS,isomer #1	CC(C)=CCC=C(C)O[Si](C)(C)C	1137.6	Standard non polar	33892256
Sulcatone,1TMS,isomer #2	C=C(CCC=C(C)C)O[Si](C)(C)C	1139.2	Semi standard non polar	33892256
Sulcatone,1TMS,isomer #2	C=C(CCC=C(C)C)O[Si](C)(C)C	1140.9	Standard non polar	33892256
Sulcatone,1TBDMS,isomer #1	CC(C)=CCC=C(C)O[Si](C)(C)C(C)(C)C	1391.2	Semi standard non polar	33892256
Sulcatone,1TBDMS,isomer #1	CC(C)=CCC=C(C)O[Si](C)(C)C(C)(C)C	1356.9	Standard non polar	33892256
Sulcatone,1TBDMS,isomer #2	C=C(CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1354.1	Semi standard non polar	33892256
Sulcatone,1TBDMS,isomer #2	C=C(CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1339.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Sulcatone EI-B (Non-derivatized)	splash10-0006-9000000000-52448d8f5e75dfce2601	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Sulcatone EI-B (Non-derivatized)	splash10-0006-9000000000-52448d8f5e75dfce2601	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulcatone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-2a4a7d0cf2baca776c97	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulcatone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9100000000-a1a351553f2efdaaf3bc	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 10V, Positive-QTOF	splash10-056r-2900000000-1c6462dfab5ba93de56a	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 20V, Positive-QTOF	splash10-0ar0-9800000000-3a5a239448b9074b6329	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 40V, Positive-QTOF	splash10-0uxr-9000000000-b4f774fa9c89ef7f85a5	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 10V, Negative-QTOF	splash10-004i-0900000000-77ea35597ceee3c16d4b	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 20V, Negative-QTOF	splash10-004i-4900000000-223aa0397cf0652e4556	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 40V, Negative-QTOF	splash10-0a4i-9200000000-7fc0a9ab1c35aabebd1a	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 10V, Positive-QTOF	splash10-00lr-9000000000-127501d70495320af54a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 20V, Positive-QTOF	splash10-00lu-9000000000-8fc1002b65f684523858	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 40V, Positive-QTOF	splash10-00kf-9000000000-795b6ce8a1b72433148f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 10V, Negative-QTOF	splash10-004i-5900000000-8f58954cc0b9f482a4e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 20V, Negative-QTOF	splash10-0a4i-2900000000-532dc780633705c5e213	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulcatone 40V, Negative-QTOF	splash10-0a4i-9000000000-8f7fbaf286a4bd19c293	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Breath
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	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24260553	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20055983	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Both	Normal	21386183	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21386183	details
Feces	Detected and Quantified	0-84075.432 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Breath	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Allergic asthma	22835687	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
Feces	Detected and Quantified	0-470986.184 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn's disease	24811995	details

Associated Disorders and Diseases

Disease References

Asthma
Caldeira M, Perestrelo R, Barros AS, Bilelo MJ, Morete A, Camara JS, Rocha SM: Allergic asthma exhaled breath metabolome: a challenge for comprehensive two-dimensional gas chromatography. J Chromatogr A. 2012 Sep 7;1254:87-97. doi: 10.1016/j.chroma.2012.07.023. Epub 2012 Jul 16. [PubMed:22835687 ]
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 ] De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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 ]
Crohn's disease
De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]

Associated OMIM IDs

600807 (Asthma)
212750 (Celiac disease)
266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sulcatone

METLIN ID

Not Available

PubChem Compound

9862

PDB ID

Not Available

ChEBI ID

16310

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008311

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 Sulcatone (HMDB0035915)

MOL for HMDB0035915 (Sulcatone)

3D MOL for HMDB0035915 (Sulcatone)

3D SDF for HMDB0035915 (Sulcatone)

3D-SDF for HMDB0035915 (Sulcatone)

PDB for HMDB0035915 (Sulcatone)

3D PDB for HMDB0035915 (Sulcatone)

SMILES for HMDB0035915 (Sulcatone)

INCHI for HMDB0035915 (Sulcatone)

Structure for HMDB0035915 (Sulcatone)

3D Structure for HMDB0035915 (Sulcatone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra