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Showing Compound Imperatorin (FDB012752)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:32 UTC
Primary IDFDB012752
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameImperatorin
DescriptionImperatorin, also known as ammidin or marmelosin, belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Imperatorin is an extremely weak basic (essentially neutral) compound (based on its pKa). Imperatorin is found, on average, in the highest concentration in a few different foods, such as parsnips, lovages, and parsley and in a lower concentration in fennels. Imperatorin has also been detected, but not quantified in, several different foods, such as lambsquarters, fruits, dills, anises, and limes. This could make imperatorin a potential biomarker for the consumption of these foods. Imperatorin is a potentially toxic compound.
CAS Number482-44-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
8-IsoamylenoxypsoralenChEBI
8-IsopentenyloxypsoraleneChEBI
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]-1-benzopyran-7-oneChEBI
AmmidinChEBI
MarmelosinChEBI
PentosalenChEBI
5-Hydroxy-8-(1,1-dimethylallyl)psoralenHMDB
9-(3-Methyl-2-butenyloxy)-7-oxofuro[3,2-g]chromeneHMDB
9-(3-Methylbut-2-enyloxy)-7H-furo(3,2-g)chromen-7-oneHMDB
9-(3-Methylbut-2-enyloxy)furo[3,2-g]chromen-7-oneHMDB
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ciHMDB
9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-oneHMDB
MarmelideHMDB
Pentasalen, banHMDB
5-hydroxy-8-(1,1-dimethylallyl)psoralenbiospider
8-isoamylenoxypsoralenbiospider
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-onebiospider
Pentasalen, BANdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP3.62ALOGPS
logP3.15ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.97 m³·mol⁻¹ChemAxon
Polarizability28.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H14O4
IUPAC name9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3
InChI KeyOLOOJGVNMBJLLR-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2
Average Molecular Weight270.28
Monoisotopic Molecular Weight270.089208936
Classification
Description belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.10%; H 5.22%; O 23.68%DFC
Melting PointMp 102°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data301 (e 10600) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0q4l-5490000000-8addd2b7e7d5a89c1657JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090000000-205792cde142f77aa94fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9080000000-7795cfce5b3fcd729d41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9540000000-7130c7ebffd168204435JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6f0805a46d8f54b963d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-cdea20e125d3564dc0caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1920000000-a1c90224178c9971284dJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0udi-3290000000-ccce724ec532a9b1c7aeJSpectraViewer | MoNA
ChemSpider ID9797
ChEMBL IDCHEMBL453805
KEGG Compound IDC09269
Pubchem Compound ID10212
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34376
CRC / DFC (Dictionary of Food Compounds) IDHKP35-Z:HKP35-Z
EAFUS IDNot Available
Dr. Duke IDIMPERATORIN
BIGG IDNot Available
KNApSAcK IDC00002477
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDImperatorin
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 aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti aggregantDUKE
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukodermicDUKE
anti mitoticDUKE
anti mutagenicDUKE
anti plateletDUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti vitiligicDUKE
bufocideDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytochrome-P450 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
diabetic-macular-edema inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
lipolyticDUKE
molluscicide33904 A substance used to destroy pests of the phylum Mollusca.DUKE
piscicideDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
acetylcholinesterase inhibitor38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).