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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:12:04 UTC
Update Date2021-10-13 06:40:55 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 found, on average, in the highest concentration within a few different foods, such as parsnips (Pastinaca sativa), lovages (Levisticum officinale), and parsleys (Petroselinum crispum) and in a lower concentration in fennels (Foeniculum vulgare). Imperatorin has also been detected, but not quantified in, several different foods, such as lemons (Citrus limon), root vegetables, anises (Pimpinella anisum), lambsquarters (Chenopodium album), and wild celeries (Apium graveolens). This could make imperatorin a potential biomarker for the consumption of these foods. Imperatorin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Imperatorin.
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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point102 °CNot Available
Boiling Point448.00 to 449.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility635.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.983 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP10(3.62) g/LALOGPS
logP10(3.15) g/LChemAxon
logS10(-3.9) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.08431661259
DarkChem[M-H]-162.30431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Imperatorin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0q4l-5490000000-8addd2b7e7d5a89c16572017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imperatorin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-3290000000-ccce724ec532a9b1c7ae2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Imperatorin 40V, Positive-QTOFsplash10-0002-2900000000-a48f50b827aed0c2c74e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imperatorin 20V, Positive-QTOFsplash10-0udi-1390000000-a4331e3b6e6ab9ba18c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imperatorin 10V, Positive-QTOFsplash10-0udi-1090000000-25f99a63f2c9348d28052021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 10V, Positive-QTOFsplash10-00di-1090000000-205792cde142f77aa94f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 20V, Positive-QTOFsplash10-014i-9080000000-7795cfce5b3fcd729d412016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 40V, Positive-QTOFsplash10-0uxu-9540000000-7130c7ebffd1682044352016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 10V, Negative-QTOFsplash10-014i-0090000000-6f0805a46d8f54b963d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 20V, Negative-QTOFsplash10-0udi-0290000000-cdea20e125d3564dc0ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 40V, Negative-QTOFsplash10-0a4i-1920000000-a1c90224178c9971284d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 10V, Positive-QTOFsplash10-0udi-0090000000-2e5a86e101fa40f235c92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 20V, Positive-QTOFsplash10-0udi-0190000000-58ef289697c902aee31e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 40V, Positive-QTOFsplash10-004i-2950000000-6ffc6c72bc8380498c4d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 10V, Negative-QTOFsplash10-0gb9-0090000000-e4734d549fe36cc622022021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 20V, Negative-QTOFsplash10-0udi-0090000000-3a57f1382615518fb5d12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imperatorin 40V, Negative-QTOFsplash10-0uk9-0790000000-eef12a3af90025252e5c2021-09-23Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1027431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .