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Showing Compound Isoimperatorin (FDB003953)

Record Information
Version1.0
Creation date2010-04-08 22:06:01 UTC
Update date2025-11-18 22:54:28 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
MOLSDFPDBSMILESInChI
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
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-8290000000-27260c39496d6e0b62512014-09-20View Spectrum
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-0290000000-6fc9699eb703287cc20c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-91b67568346d3505ed842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0005-5900000000-456019d3d6f24671b66c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-b0c02d050a925e7d55772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-3590000000-9f0a858c5257f0f683412021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0wos-5960000000-45ec8597e6a51c9b31ac2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090000000-8ac6c0a5fb70291a1eaa2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9080000000-6df3f42b8b7e78aa7f2d2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9530000000-fb7bbc5a1973fd1a795d2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-300965788bf7c4527eb02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-9161a37ce9657cf9058e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0910000000-ff19b981b89111d7fcb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-2e5a86e101fa40f235c92021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-2e5a86e101fa40f235c92021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-1940000000-e7dafddba6e1b25841752021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d3eedc6d74870144d16f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-55d1bfdb46af46eb41172021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2930000000-85deed983716c2656d622021-10-12View Spectrum
NMR
TypeDescriptionView
ChemSpider ID61393
ChEMBL IDCHEMBL448060
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 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
ArtemicideAn herbicidal agent that targets and eliminates weeds of the Artemisia genus, with potential therapeutic applications in allergy management and anti-inflammatory uses, particularly for conditions exacerbated by Artemisia allergens.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cytochrome-P450 inhibitor50183 An agent that blocks the activity of cytochrome-P450 enzymes, reducing drug metabolism. Therapeutically, it's used to increase the efficacy of certain medications, manage drug interactions, and treat conditions like erectile dysfunction, by inhibiting the breakdown of key drugs, allowing them to remain active in the body for a longer period.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Diabetic-macular-edema inhibitor35222 An agent that reduces fluid accumulation in the macula, alleviating vision impairment in diabetic patients. It blocks vascular endothelial growth factor (VEGF) activity, decreasing inflammation and edema, commonly used to treat diabetic macular edema and other retinal disorders.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Acetylcholinesterase inhibitor38462 An agent that blocks the breakdown of acetylcholine, increasing its concentration and enhancing cholinergic transmission. Therapeutically, it improves cognitive function and muscle contraction, commonly used in managing Alzheimer's disease, myasthenia gravis, and glaucoma.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).