Record Information
Version1.0
Creation date2010-04-08 22:10:24 UTC
Update date2018-05-28 23:39:43 UTC
Primary IDFDB012857
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNeocnidilide
DescriptionNeocnidilide, also known as sedanolide, belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. Neocnidilide is an extremely weak basic (essentially neutral) compound (based on its pKa). Neocnidilide is a herbal tasting compound. Neocnidilide is found, on average, in the highest concentration in wild celeries. Neocnidilide has also been detected, but not quantified in, a few different foods, such as corianders, dills, and green vegetables. This could make neocnidilide a potential biomarker for the consumption of these foods.
CAS Number4567-33-3
Structure
Thumb
Synonyms
SynonymSource
3-Butyl-3a,4,5,6-tetrahydro-1(3H)-isobenzofuranone, 9ciHMDB
SedanolideHMDB
NeocnidilideMeSH
Neocnidilide, cis-(-)-isomerMeSH
Neocnidilide, (trans)-isomerMeSH
Neocnidilide, (cis)-isomerMeSH
3-Butyl-3a,4,5,6-tetrahydro-1(3H)-isobenzofuranone, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP3.28ALOGPS
logP3.39ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.77 m³·mol⁻¹ChemAxon
Polarizability22.52 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H18O2
IUPAC name3-butyl-1,3,3a,4,5,6-hexahydro-2-benzofuran-1-one
InChI IdentifierInChI=1S/C12H18O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h7,9,11H,2-6,8H2,1H3
InChI KeyUPJFTVFLSIQQAV-UHFFFAOYSA-N
Isomeric SMILESCCCCC1OC(=O)C2=CCCCC12
Average Molecular Weight194.2701
Monoisotopic Molecular Weight194.13067982
Classification
Description belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsobenzofurans
Sub ClassNot Available
Direct ParentIsobenzofurans
Alternative Parents
Substituents
  • Isobenzofuran
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.19%; H 9.34%; O 16.47%DFC
Melting PointMp 34.5-35° (24-27°)DFC
Boiling PointBp0.4 112°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -74.7 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00nf-7900000000-15d786d7601d8b44b203JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-d39a7ef515fc66b140c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-7900000000-eacd70bed5997c596974JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-9100000000-830232c52182598f582cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-cb068c432eb0727709e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-1900000000-93b3dde9e3e983c129d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-9600000000-d8f8b9313f8bdb98b622JSpectraViewer
ChemSpider ID4197506
ChEMBL IDNot Available
KEGG Compound IDC17002
Pubchem Compound ID5018391
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34450
CRC / DFC (Dictionary of Food Compounds) IDHMN48-J:HMN48-J
EAFUS IDNot Available
Dr. Duke IDSEDANOLIDE|NEOCNIDILIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1069401
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).