Showing Compound Imperatorin (FDB012752)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:20 UTC

Update date

2019-11-26 03:07:32 UTC

Primary ID

FDB012752

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Imperatorin

Description

Imperatorin, 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). 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 lambsquarters, dills, limes, fruits, and lemons. This could make imperatorin a potential biomarker for the consumption of these foods. Imperatorin is a potentially toxic compound.

CAS Number

482-44-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
8-Isoamylenoxypsoralen	ChEBI
8-Isopentenyloxypsoralene	ChEBI
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]-1-benzopyran-7-one	ChEBI
Ammidin	ChEBI
Marmelosin	ChEBI
Pentosalen	ChEBI
5-Hydroxy-8-(1,1-dimethylallyl)psoralen	HMDB
9-(3-Methyl-2-butenyloxy)-7-oxofuro[3,2-g]chromene	HMDB
9-(3-Methylbut-2-enyloxy)-7H-furo(3,2-g)chromen-7-one	HMDB
9-(3-Methylbut-2-enyloxy)furo[3,2-g]chromen-7-one	HMDB
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ci	HMDB
9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one	HMDB
Marmelide	HMDB
Pentasalen, ban	HMDB
5-hydroxy-8-(1,1-dimethylallyl)psoralen	biospider
8-isoamylenoxypsoralen	biospider
9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9CI	db_source
9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one	biospider
Pentasalen, BAN	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.15	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.97 m³·mol⁻¹	ChemAxon
Polarizability	28.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H14O4

IUPAC name

9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

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 Key

OLOOJGVNMBJLLR-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:5885 )
Furanocoumarins (C09269 )

Ontology

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Anticonvulsant

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 71.10%; H 5.22%; O 23.68%	DFC
Melting Point	Mp 102°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	301 (e 10600) (MeOH)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0udi-3290000000-ccce724ec532a9b1c7ae	Spectrum
Predicted GC-MS	Imperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0q4l-5490000000-8addd2b7e7d5a89c1657	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1090000000-205792cde142f77aa94f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9080000000-7795cfce5b3fcd729d41	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9540000000-7130c7ebffd168204435	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-6f0805a46d8f54b963d2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0290000000-cdea20e125d3564dc0ca	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1920000000-a1c90224178c9971284d	Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34376

CRC / DFC (Dictionary of Food Compounds) ID

HKP35-Z:HKP35-Z

EAFUS ID

Not Available

Dr. Duke ID

IMPERATORIN

BIGG ID

Not Available

KNApSAcK ID

C00002477

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Imperatorin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti aggregant			DUKE
anti alopecic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukodermic			DUKE
anti mitotic			DUKE
anti mutagenic			DUKE
anti platelet			DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti vitiligic			DUKE
bufocide			DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cytochrome-P450 inhibitor	50183	An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.	DUKE
diabetic-macular-edema inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hepatotoxic	50908	A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.	DUKE
lipolytic			DUKE
molluscicide	33904	A substance used to destroy pests of the phylum Mollusca.	DUKE
piscicide			DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
acetylcholinesterase inhibitor	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	CHEBI