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Showing Compound Imperatorin (FDB012752)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:32 UTC
Primary IDFDB012752
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 root vegetables, limes (Citrus aurantiifolia), fruits, lemons (Citrus limon), and lambsquarters (Chenopodium album). This could make imperatorin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Imperatorin.
CAS Number482-44-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
5-hydroxy-8-(1,1-dimethylallyl)psoralenbiospider
8-isoamylenoxypsoralenbiospider
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-onebiospider
Pentasalen, BANdb_source
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
Chemical FormulaC16H14O4
IUPAC name9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(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
Isomeric SMILESCC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.10%; H 5.22%; O 23.68%DFC
Melting PointMp 102°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data301 (e 10600) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-3290000000-ccce724ec532a9b1c7ae2014-09-20View Spectrum
Predicted GC-MSImperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0q4l-5490000000-8addd2b7e7d5a89c1657Spectrum
Predicted GC-MSImperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-2900000000-a48f50b827aed0c2c74e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1390000000-a4331e3b6e6ab9ba18c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1090000000-25f99a63f2c9348d28052021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1090000000-205792cde142f77aa94f2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9080000000-7795cfce5b3fcd729d412016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9540000000-7130c7ebffd1682044352016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6f0805a46d8f54b963d22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-cdea20e125d3564dc0ca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1920000000-a1c90224178c9971284d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-2e5a86e101fa40f235c92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0190000000-58ef289697c902aee31e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2950000000-6ffc6c72bc8380498c4d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0090000000-e4734d549fe36cc622022021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-3a57f1382615518fb5d12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-0790000000-eef12a3af90025252e5c2021-09-23View Spectrum
NMR
TypeDescriptionView
ChemSpider ID9797
ChEMBL IDCHEMBL453805
KEGG Compound IDC09269
Pubchem Compound ID10212
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34376
CRC / DFC (Dictionary of Food Compounds) IDHKP35-Z:HKP35-Z
EAFUS IDNot Available
Dr. Duke IDIMPERATORIN
BIGG IDNot Available
KNApSAcK IDC00002477
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDImperatorin
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
Anti aflatoxin35222 An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-alopecic52217 An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth.DUKE
Anti convulsant52217 An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti leukodermicAn agent that treats leucoderma (vitiligo), characterized by white skin patches or total loss of pigmentation, promoting skin repigmentation and reducing disease progression, commonly used in dermatology to manage vitiligo and other skin pigmentation disorders.DUKE
Anti mitoticAn agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti plateletAn agent that prevents blood clot formation by inhibiting platelet aggregation, used to treat and prevent heart disease, stroke, and other cardiovascular conditions.DUKE
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
Anti-vitiligicAn agent that prevents loss of skin pigmentation, characteristic of vitiligo, promoting melanocyte preservation and repigmentation, used therapeutically to manage vitiligo and other hypopigmentation disorders.DUKE
BufocideA cardiotonic steroid, bufocide plays a biological role in regulating cardiac function. Therapeutically, it has applications as a cardiostimulant and diuretic. Key medical uses include treating heart failure and edema, with potential in managing certain arrhythmias and hypertension.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
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.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
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
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
Molluscicide33904 An agent that kills mollusks, particularly snails and slugs, playing a key role in controlling vectors of parasitic diseases. Therapeutically, it is used to prevent the spread of schistosomiasis and other snail-borne diseases, with medical applications in public health and epidemiology.DUKE
PiscicideA substance poisonous to fish, used to eliminate dominant or invasive fish species, and combat parasitic fish, allowing for population control and management of aquatic ecosystems.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.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).