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Record Information
Version2.0
Created at2022-03-17 20:48:38 UTC
Updated at2022-03-17 20:48:38 UTC
NP-MRD IDNP0047953
Secondary Accession NumbersNone
Natural Product 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 within 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 wild celeries, anises, dills, fruits, and lambsquarters. This could make imperatorin a potential biomarker for the consumption of these foods. Imperatorin is a potentially toxic compound. All photobiological effects of furocoumarins result from their photochemical reactions. PON1 can inactivate some organophosphates through hydrolysis. Imperatorin is found in Aegle marmelos , Aeglopsis chevalieri, Afraegle paniculata, Allium wallichii, Ammi majus, Ammi visnaga, Amyris pinnata, Angelica archangelica , Angelica dahurica , Angelica decursiva, Angelica furcijuga KITAGAWA, Angelica keiskei, Angelica komarovii, Angelica lucida, Angelica saxatilis, Angelica sinensis , Angelica spp., Angelica taiwaniana, Angelica ursina, Angelica ursina Maxim, Aspergillus flavus, Atalantia ceylanica, Brachyclados megalanthus, Cachrys sicula, Cicerbita alpina, Citrus meyeri, Poncirus trifoliata , Clausena anisata , Clausena lansium, Cnidium monnieri , Corydalis bungeana , Daucus carota, Deverra tortuosa, Deverra triradiata, Dinosperma stipitatum, Esenbeckia grandiflora, Esenbeckia yaxhoob Lundell, Euphorbia bivonae, Ferula communis, Ferula mogoltavica, Ferula moschata, Ferula sumbul , Ferula syreitschikowii, Fragaria spp., Glehnia littoralis , Hansenia weberbaueriana, Heracleum aconitifolium, Heracleum asperum, Heracleum candicans, Heracleum canescens, Heracleum dissectum, Heracleum granatense, Heracleum mantegazzianum, Heracleum moellendorffii Hance, Heracleum moellendorffii Hance var.paucivitatum, Heracleum pinnatum, Heracleum ponticum, Heracleum rapula, Heracleum sphondylium , Heracleum spp., Heracleum woroschiklowii, Leptothyrsa sprucei, Libanotis buchtormensis, Ligusticum multivittatum, Magydaris pastinacea, Melicope triphylla, Metrodorea flavida, Murraya paniculata , Niphogeton ternata, Opopanax chironium, Oppopanax chironium, Orixa japonica , Ostericum grosseserratum, Pamburus missionis, Pastinaca spp., Peucedanum dhana, Peucedanum japonicum, Peucedanum ostruthium , Peucedanum palustre, Peucedanum rubricaule, Phebalium canaliculatum, Phebalium tuberculosum, Pleurospermum rivulorum, Prangos bucharica, Prangos didyma, Prangos ferulacea, Prangos lipskyi, Prangos lophoptera, Prangos pabularia , Prangos trifida, Prangos tschimganica, Ptelea trifolia, Rhadinothamnus rudis, Ruta graveolens, Saposhnikovia divaricata, Saposhnikovia divaricata Schischkin, Seseli tortuosum LBS.Eur., Seseli webbii Cosson., Seseli yunnanense, Skimmia japonica, Skimmia laureola, Angelica capitellata, Thamnosma rhodesica, Thamnosma texana, Tordyliopsis brunonis, Trichocline caulescens, Zanthoxylum americanum, Zanthoxylum rhoifolium, Zanthoxylum zanthoxyloides and Zeravschania regeliana. Imperatorin was first documented in 2002 (PMID: 12510838). Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.
Structure
Thumb
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 Mass270.2800 Da
Monoisotopic Mass270.08921 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aegle marmelosPlant
Aeglopsis chevalieriLOTUS Database
Afraegle paniculataLOTUS Database
Allium wallichiiLOTUS Database
Ammi majusLOTUS Database
Ammi visnagaLOTUS Database
Amyris pinnataLOTUS Database
Anethum graveolensFooDB
Angelica archangelicaPlant
Angelica dahuricaPlant
Angelica decursivaLOTUS Database
Angelica furcijuga KITAGAWAPlant
Angelica keiskeiLOTUS Database
Angelica komaroviiPlant
Angelica lucidaLOTUS Database
Angelica saxatilisLOTUS Database
Angelica sinensisPlant
Angelica spp.Plant
Angelica taiwanianaPlant
Angelica ursinaLOTUS Database
Angelica ursina MaximPlant
Apium graveolensFooDB
Aspergillus flavusFungi
Atalantia ceylanicaPlant
Brachyclados megalanthusPlant
Cachrys siculaLOTUS Database
Chenopodium albumFooDB
Cicerbita alpinaLOTUS Database
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Citrus meyeriPlant
Citrus trifoliataPlant
Clausena anisataPlant
Clausena lansiumLOTUS Database
Cnidium monnieriPlant
Corydalis bungeanaPlant
Daucus carotaLOTUS Database
Deverra tortuosaLOTUS Database
Deverra triradiataLOTUS Database
Dinosperma stipitatumLOTUS Database
Esenbeckia grandifloraLOTUS Database
Esenbeckia yaxhoob LundellPlant
Euphorbia bivonaeLOTUS Database
Ferula communisLOTUS Database
Ferula mogoltavicaLOTUS Database
Ferula moschataLOTUS Database
Ferula sumbulPlant
Ferula syreitschikowiiPlant
Foeniculum vulgareFooDB
Fragaria spp.Plant
Glehnia littoralisPlant
Hansenia weberbauerianaLOTUS Database
Heracleum aconitifoliumLOTUS Database
Heracleum asperumPlant
Heracleum candicansLOTUS Database
Heracleum canescensPlant
Heracleum dissectumPlant
Heracleum granatensePlant
Heracleum mantegazzianumLOTUS Database
Heracleum moellendorffii HancePlant
Heracleum moellendorffii Hance var.paucivitatumPlant
Heracleum pinnatumPlant
Heracleum ponticumPlant
Heracleum rapulaLOTUS Database
Heracleum sphondyliumPlant
Heracleum spp.Plant
Heracleum woroschiklowiiPlant
Leptothyrsa spruceiPlant
Levisticum officinaleFooDB
Libanotis buchtormensisLOTUS Database
Ligusticum multivittatumPlant
Magydaris pastinaceaLOTUS Database
Melicope triphyllaLOTUS Database
Metrodorea flavidaLOTUS Database
Murraya paniculataPlant
Niphogeton ternataPlant
Opopanax chironiumPlant
Oppopanax chironium-
Orixa japonicaPlant
Ostericum grosseserratumLOTUS Database
Pamburus missionisLOTUS Database
Pastinaca sativaFooDB
Pastinaca spp.Plant
Petroselinum crispumFooDB
Peucedanum dhanaPlant
Peucedanum japonicumLOTUS Database
Peucedanum ostruthiumPlant
Peucedanum palustreLOTUS Database
Peucedanum rubricaulePlant
Phebalium canaliculatumLOTUS Database
Phebalium tuberculosumLOTUS Database
Pimpinella anisumFooDB
Pleurospermum rivulorumPlant
Prangos bucharicaPlant
Prangos didymaLOTUS Database
Prangos ferulaceaLOTUS Database
Prangos lipskyiLOTUS Database
Prangos lophopteraLOTUS Database
Prangos pabulariaPlant
Prangos trifidaLOTUS Database
Prangos tschimganicaLOTUS Database
Ptelea trifoliaPlant
Rhadinothamnus rudisLOTUS Database
Ruta graveolensLOTUS Database
Saposhnikovia divaricataLOTUS Database
Saposhnikovia divaricata SchischkinPlant
Seseli tortuosum LBS.Eur.Plant
Seseli webbii Cosson.Plant
Seseli yunnanensePlant
Skimmia japonicaLOTUS Database
Skimmia laureolaLOTUS Database
Sphenosciadium capitellatumLOTUS Database
Thamnosma rhodesicaLOTUS Database
Thamnosma texanaLOTUS Database
Tordyliopsis brunonisLOTUS Database
Trichocline caulescensLOTUS Database
Zanthoxylum americanumLOTUS Database
Zanthoxylum rhoifoliumLOTUS Database
Zanthoxylum zanthoxyloidesLOTUS Database
Zeravschania regelianaLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0034376
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
Good Scents IDNot Available
References
General References
  1. Kim DK, Lim JP, Yang JH, Eom DO, Eun JS, Leem KH: Acetylcholinesterase inhibitors from the roots of Angelica dahurica. Arch Pharm Res. 2002 Dec;25(6):856-9. doi: 10.1007/BF02977004. [PubMed:12510838 ]