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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:12:04 UTC
Update Date2019-07-23 06:15:54 UTC
HMDB IDHMDB0034376
Secondary Accession Numbers
  • HMDB34376
Metabolite Identification
Common 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). Outside of the human body, 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 root vegetables, lambsquarters, dills, wild celeries, and fruits. This could make imperatorin a potential biomarker for the consumption of these foods. Imperatorin is a potentially toxic compound. It displays a significant preference for PDE4B over PDE4A. It is biosynthesized from umbelliferone, a coumarin derivative. Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L (Malvaceae), Angelica archangelica, Angelica dahurica, Glehnia littoralis, Saposhnikovia divaricata, Cnidium monnieri, Incarvillea younghusbandii, and Zanthoxylum americanum mill. The procedure for the isolation of imperatorin from Urena lobata involves exhaustively extracting under reflux with benzene the air-dried and pulverised roots followed by separation by column chromatography. Imperatorin was identified from a Bioactive Molecules library in a high throughput screening experiment for inhibitors of the phosphodiesterase PDE4.
Structure
Data?1563862554
Synonyms
ValueSource
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
Chemical FormulaC16H14O4
Average Molecular Weight270.28
Monoisotopic Molecular Weight270.089208936
IUPAC Name9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
Traditional Nameimperatorin
CAS Registry Number482-44-0
SMILES
CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0q4l-5490000000-8addd2b7e7d5a89c1657Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090000000-205792cde142f77aa94fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9080000000-7795cfce5b3fcd729d41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9540000000-7130c7ebffd168204435Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6f0805a46d8f54b963d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-cdea20e125d3564dc0caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1920000000-a1c90224178c9971284dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-3290000000-ccce724ec532a9b1c7aeSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012752
KNApSAcK IDC00002477
Chemspider ID9797
KEGG Compound IDC09269
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImperatorin
METLIN IDNot Available
PubChem Compound10212
PDB IDNot Available
ChEBI ID5885
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang Y, Cao Y, Zhan Y, Duan H, He L: Furanocoumarins-imperatorin inhibits myocardial hypertrophy both in vitro and in vivo. Fitoterapia. 2010 Dec;81(8):1188-95. doi: 10.1016/j.fitote.2010.07.023. Epub 2010 Aug 4. [PubMed:20691250 ]
  2. Luszczki JJ, Andres-Mach M, Glensk M, Skalicka-Wozniak K: Anticonvulsant effects of four linear furanocoumarins, bergapten, imperatorin, oxypeucedanin, and xanthotoxin, in the mouse maximal electroshock-induced seizure model: a comparative study. Pharmacol Rep. 2010 Nov-Dec;62(6):1231-6. [PubMed:21273683 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .