AFCDB: 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 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 Number

482-44-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 71.10%; H 5.22%; O 23.68%	DFC
Melting Point	Mp 102°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0udi-3290000000-ccce724ec532a9b1c7ae	2014-09-20	View Spectrum
Predicted GC-MS	Imperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0q4l-5490000000-8addd2b7e7d5a89c1657	Spectrum
Predicted GC-MS	Imperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-2900000000-a48f50b827aed0c2c74e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1390000000-a4331e3b6e6ab9ba18c6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1090000000-25f99a63f2c9348d2805	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1090000000-205792cde142f77aa94f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9080000000-7795cfce5b3fcd729d41	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxu-9540000000-7130c7ebffd168204435	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-6f0805a46d8f54b963d2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0290000000-cdea20e125d3564dc0ca	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1920000000-a1c90224178c9971284d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-2e5a86e101fa40f235c9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0190000000-58ef289697c902aee31e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-2950000000-6ffc6c72bc8380498c4d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0090000000-e4734d549fe36cc62202	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-3a57f1382615518fb5d1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-0790000000-eef12a3af90025252e5c	2021-09-23	View 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

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Search:

Food	Content Range	Average	Reference

Dill	Expected but not quantified	Not Available	DUKE
Parsnip	170.000 - 170.000	170.000	DUKE

Showing 1 to 2 of 2 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Search:

Descriptor	ID	Definition	Reference
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
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

Showing 1 to 10 of 23 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Imperatorin (FDB012752)

Structure for FDB012752 (Imperatorin)