Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 20:57:49 UTC
Update Date2022-03-07 02:54:42 UTC
HMDB IDHMDB0035915
Secondary Accession Numbers
  • HMDB35915
Metabolite Identification
Common NameSulcatone
DescriptionSulcatone, 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
Data?1589383154
Synonyms
ValueSource
6-Methyl-5-hepten-2-oneChEBI
6-Methylhept-5-en-2-oneChEBI
MethylheptenoneKegg
2-Methyl-2-hepten-6-oneHMDB
2-Methyl-6-heptenoneHMDB
2-Methyl-6-oxo-2-hepteneHMDB
2-Methylhept-2-en-6-oneHMDB
2-oxo-6-Methylhept-5-eneHMDB
6-Methyl hept-5-en-2-oneHMDB
6-Methyl-5-heptene-2-oneHMDB
6-Methylheptan-5-ene-2-oneHMDB
FEMA 2707HMDB
PrenylacetoneHMDB
6-Methylhept-5-ene-2-oneHMDB
SulcatoneMeSH
Chemical FormulaC8H14O
Average Molecular Weight126.1962
Monoisotopic Molecular Weight126.10446507
IUPAC Name6-methylhept-5-en-2-one
Traditional Name6-methyl-5-hepten-2-one
CAS Registry Number110-93-0
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 KeyUHEPJGULSIKKTP-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-67 °CNot Available
Boiling Point72.00 to 73.00 °C. @ 18.00 mm HgThe Good Scents Company Information System
Water Solubility3351 /mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP1.947 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.54 g/LALOGPS
logP2.01ALOGPS
logP2.02ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.02 m³·mol⁻¹ChemAxon
Polarizability15.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.05631661259
DarkChem[M-H]-124.97531661259
DeepCCS[M+H]+131.930932474
DeepCCS[M-H]-129.70630932474
DeepCCS[M-2H]-165.81130932474
DeepCCS[M+Na]+140.63130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulcatoneCC(C)=CCCC(C)=O1308.9Standard polar33892256
SulcatoneCC(C)=CCCC(C)=O959.3Standard non polar33892256
SulcatoneCC(C)=CCCC(C)=O974.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulcatone,1TMS,isomer #1CC(C)=CCC=C(C)O[Si](C)(C)C1184.4Semi standard non polar33892256
Sulcatone,1TMS,isomer #1CC(C)=CCC=C(C)O[Si](C)(C)C1137.6Standard non polar33892256
Sulcatone,1TMS,isomer #2C=C(CCC=C(C)C)O[Si](C)(C)C1139.2Semi standard non polar33892256
Sulcatone,1TMS,isomer #2C=C(CCC=C(C)C)O[Si](C)(C)C1140.9Standard non polar33892256
Sulcatone,1TBDMS,isomer #1CC(C)=CCC=C(C)O[Si](C)(C)C(C)(C)C1391.2Semi standard non polar33892256
Sulcatone,1TBDMS,isomer #1CC(C)=CCC=C(C)O[Si](C)(C)C(C)(C)C1356.9Standard non polar33892256
Sulcatone,1TBDMS,isomer #2C=C(CCC=C(C)C)O[Si](C)(C)C(C)(C)C1354.1Semi standard non polar33892256
Sulcatone,1TBDMS,isomer #2C=C(CCC=C(C)C)O[Si](C)(C)C(C)(C)C1339.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sulcatone EI-B (Non-derivatized)splash10-0006-9000000000-52448d8f5e75dfce26012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sulcatone EI-B (Non-derivatized)splash10-0006-9000000000-52448d8f5e75dfce26012018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulcatone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-2a4a7d0cf2baca776c972016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulcatone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-a1a351553f2efdaaf3bc2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 10V, Positive-QTOFsplash10-056r-2900000000-1c6462dfab5ba93de56a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 20V, Positive-QTOFsplash10-0ar0-9800000000-3a5a239448b9074b63292015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 40V, Positive-QTOFsplash10-0uxr-9000000000-b4f774fa9c89ef7f85a52015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 10V, Negative-QTOFsplash10-004i-0900000000-77ea35597ceee3c16d4b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 20V, Negative-QTOFsplash10-004i-4900000000-223aa0397cf0652e45562015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 40V, Negative-QTOFsplash10-0a4i-9200000000-7fc0a9ab1c35aabebd1a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 10V, Positive-QTOFsplash10-00lr-9000000000-127501d70495320af54a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 20V, Positive-QTOFsplash10-00lu-9000000000-8fc1002b65f6845238582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 40V, Positive-QTOFsplash10-00kf-9000000000-795b6ce8a1b72433148f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 10V, Negative-QTOFsplash10-004i-5900000000-8f58954cc0b9f482a4e02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 20V, Negative-QTOFsplash10-0a4i-2900000000-532dc780633705c5e2132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulcatone 40V, Negative-QTOFsplash10-0a4i-9000000000-8f7fbaf286a4bd19c2932021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-84075.432 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedAllergic asthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0-470986.184 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
Asthma
  1. 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
  1. 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 ]
  2. 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
  1. 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
  1. 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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004925
KNApSAcK IDC00011400
Chemspider ID9478
KEGG Compound IDC07287
BioCyc IDCPD-7969
BiGG IDNot Available
Wikipedia LinkSulcatone
METLIN IDNot Available
PubChem Compound9862
PDB IDNot Available
ChEBI ID16310
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008311
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .