Record Information
Version1.0
Creation date2010-04-08 22:06:01 UTC
Update date2019-11-26 02:59:42 UTC
Primary IDFDB003953
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoimperatorin
DescriptionIsoimperatorin is a member of the class of compounds known as psoralens. Psoralens 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. Isoimperatorin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Isoimperatorin can be found in a number of food items such as parsley, lime, wild celery, and parsnip, which makes isoimperatorin a potential biomarker for the consumption of these food products. Isoimperatorin is a non-carcinogenic (not listed by IARC) potentially toxic compound. If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally (T3DB).
CAS Number482-45-1
Structure
Thumb
Synonyms
SynonymSource
7,4-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]-1-benzopyran-7-oneChEBI
iso-ImperatorinMeSH
4-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]chromen-7-onebiospider
Iso-imperatorinbiospider
Isoimperatorinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP3.67ALOGPS
logP3.15ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.97 m³·mol⁻¹ChemAxon
Polarizability28.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H14O4
IUPAC name4-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C16H14O4/c1-10(2)5-7-19-16-11-3-4-15(17)20-14(11)9-13-12(16)6-8-18-13/h3-6,8-9H,7H2,1-2H3
InChI KeyIGWDEVSBEKYORK-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCOC1=C2C=CC(=O)OC2=CC2=C1C=CO2
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 Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0uxr-8290000000-27260c39496d6e0b6251Spectrum
Predicted GC-MSIsoimperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-5390000000-1bf0c24c340b994423c5Spectrum
Predicted GC-MSIsoimperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0290000000-6fc9699eb703287cc20cSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-91b67568346d3505ed84Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0005-5900000000-456019d3d6f24671b66cSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-b0c02d050a925e7d5577Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-3590000000-9f0a858c5257f0f68341Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0wos-5960000000-45ec8597e6a51c9b31acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090000000-8ac6c0a5fb70291a1eaaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9080000000-6df3f42b8b7e78aa7f2dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9530000000-fb7bbc5a1973fd1a795dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-300965788bf7c4527eb0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-9161a37ce9657cf9058eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0910000000-ff19b981b89111d7fcb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-2e5a86e101fa40f235c9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-2e5a86e101fa40f235c9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-1940000000-e7dafddba6e1b2584175Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d3eedc6d74870144d16fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-55d1bfdb46af46eb4117Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2930000000-85deed983716c2656d62Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC16976
Pubchem Compound ID68081
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDISOIMPERATORIN
BIGG IDNot Available
KNApSAcK IDC00030532
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
artemicideDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cytochrome-P450 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
diabetic-macular-edema inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).