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Showing metabocard for 4-Methyl-3-penten-2-one, 9CI (HMDB0031563)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:04 UTC
Update Date2019-07-23 06:09:01 UTC
HMDB IDHMDB0031563
Secondary Accession Numbers
  • HMDB31563
Metabolite Identification
Common Name4-Methyl-3-penten-2-one, 9CI
Description4-Methyl-3-penten-2-one, 9CI, also known as isopropylidene acetone or (CH3)2C=chc(=o)CH3, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, 4-methyl-3-penten-2-one, 9CI is considered to be an oxygenated hydrocarbon lipid molecule. 4-Methyl-3-penten-2-one, 9CI is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Methyl-3-penten-2-one, 9CI is a sweet, acrylic, and chemical tasting compound. Outside of the human body, 4-Methyl-3-penten-2-one, 9CI has been detected, but not quantified in, several different foods, such as orange bell peppers, pepper (c. frutescens), herbs and spices, yellow bell peppers, and green bell peppers. This could make 4-methyl-3-penten-2-one, 9CI a potential biomarker for the consumption of these foods. 4-Methyl-3-penten-2-one, 9CI is a potentially toxic compound. 4-Methyl-3-penten-2-one, 9CI, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1563862141
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(CH3)2C=chc(=o)CH3HMDB
1-Methylpent-2-en-4-oneHMDB
2,2-Dimethylvinyl methyl ketoneHMDB
2-Methyl-2-penten-4-oneHMDB
2-Methyl-2-pentenone-4HMDB
2-Methyl-4-oxo-2-penteneHMDB
3-Isohexen-2-oneHMDB
3-PENTEN,2-one,4-methyl mesityloxideHMDB
4-Methyl-3-penten-2-ONHMDB
4-Methyl-3-penten-2-oneHMDB
4-Methyl-3-penten-2-one (mesityl oxide)HMDB
4-Methyl-3-pentene-2-oneHMDB
4-Methylpent-3-en-2-oneHMDB
4-Metil-3-penten-2-oneHMDB
FEMA 3368HMDB
Isobutenyl methyl ketoneHMDB
Isopropylidene acetoneHMDB
Isopropylidene-acetoneHMDB
IsopropylideneacetoneHMDB
Mesityl oxideHMDB
MesityloxidHMDB
MesityloxydeHMDB
Methyl 2,2-dimethylvinyl ketoneHMDB
Methyl 2-methyl-1-propenyl ketoneHMDB
Methyl isobutenyl ketoneHMDB
Ossido di mesitileHMDB
Oxyde de mesityleHMDB
Chemical FormulaC6H10O
Average Molecular Weight98.143
Monoisotopic Molecular Weight98.073164942
IUPAC Name4-methylpent-3-en-2-one
Traditional Namemesityl oxide
CAS Registry Number141-79-7
SMILES
CC(C)=CC(C)=O
InChI Identifier
InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3
InChI KeySHOJXDKTYKFBRD-UHFFFAOYSA-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'.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnones
Alternative Parents
Substituents
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-41.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility28.9 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility20.5 g/LALOGPS
logP1.01ALOGPS
logP1.49ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.8 m³·mol⁻¹ChemAxon
Polarizability11.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7i-9000000000-3661666f8de0c561e186Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2ccSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7i-9000000000-3661666f8de0c561e186Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2ccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0536-9000000000-2812ff25d24931b41744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9000000000-1cada987a9858a217a77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-9000000000-e609ed7c7875fbd22551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-9000000000-fe1499144a8401242c76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-623d2802baf709699403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-9000000000-16572bb315d857e26b9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-9000000000-59b1a0eada94cc3c451eSpectrum
MSMass Spectrum (Electron Ionization)splash10-053s-9000000000-6fe7e7a277af44176ff4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008178
KNApSAcK IDNot Available
Chemspider ID8526
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8858
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .