AFCDB: Psoralen (FDB012605)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:16 UTC

Update date

2019-11-26 03:07:11 UTC

Primary ID

FDB012605

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Psoralen

Description

Psoralen, also known as ficusin or manaderm, 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. Psoralen is found, on average, in the highest concentration within a few different foods, such as figs (Ficus carica), parsleys (Petroselinum crispum), and parsnips (Pastinaca sativa) and in a lower concentration in fennels (Foeniculum vulgare), lovages (Levisticum officinale), and wild carrots (Daucus carota). Psoralen has also been detected, but not quantified in, several different foods, such as kales (Brassica napus var. pabularia), persian limes (Citrus latifolia), cereals and cereal products, japanese pumpkins (Cucurbita maxima), and climbing beans (Vigna umbellata). This could make psoralen a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Psoralen.

CAS Number

66-97-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.15	ALOGPS
logP	1.94	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.39 m³·mol⁻¹	ChemAxon
Polarizability	18.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H6O3

IUPAC name

7H-furo[3,2-g]chromen-7-one

InChI Identifier

InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H

InChI Key

ZCCUUQDIBDJBTK-UHFFFAOYSA-N

Isomeric SMILES

O=C1OC2=CC3=C(C=CO3)C=C2C=C1

Average Molecular Weight

186.166

Monoisotopic Molecular Weight

186.031694053

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
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:27616 )
Furanocoumarins (C09305 )
a small molecule (PHYTOALEXIN-CMPD )

Ontology

Physiological effect

Health effect:

Health condition:

Skin and subcutaneous tissue disorders:

Erythema

Observation:

Edema

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Anti-histamine

Biological role:

Nutrient

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	1.67	(IN PRESS)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 70.97%; H 3.25%; O 25.78%	DFC
Melting Point	Mp 171° (161-162°, 165°)	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)	splash10-052r-3900000000-eff7b2146482de5c7740	2014-09-20	View Spectrum
GC-MS	Psoralen, non-derivatized, GC-MS Spectrum	splash10-0pbi-0900000000-f4158c6b7c0ecf20d9fe	Spectrum
GC-MS	Psoralen, non-derivatized, GC-MS Spectrum	splash10-0r2i-6900000000-276c6db470fc13777449	Spectrum
GC-MS	Psoralen, non-derivatized, GC-MS Spectrum	splash10-0pbi-0900000000-f4158c6b7c0ecf20d9fe	Spectrum
GC-MS	Psoralen, non-derivatized, GC-MS Spectrum	splash10-0r2i-6900000000-276c6db470fc13777449	Spectrum
Predicted GC-MS	Psoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052u-1900000000-900e13490ddfba7e89ef	Spectrum
Predicted GC-MS	Psoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Psoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00lr-1900000000-ac91ad62c36a29665a71	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-75211365e04f08273288	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00lr-0900000000-fa9d08e8d5421ebeaa77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0f89-0900000000-bacd49139ec536fb55e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-1900000000-ac91ad62c36a29665a71	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-001r-0900000000-195d9e7e3b29cf95c327	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-75211365e04f08273288	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0900000000-fa9d08e8d5421ebeaa77	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-0900000000-bacd49139ec536fb55e7	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-287480067e742345fcb9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-2bf4a5ffe9d6883b015e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-1900000000-519db61c8cb6a8a31549	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-559cba64d14574cb0041	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-503a6a3d5ba551e5c0f5	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-857f114f045cf9aa2b39	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-f3f07adc83a68e9e76ff	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f3f07adc83a68e9e76ff	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-a2c2c14d0cf6b23ada92	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-89e4df10d3690e5a6d15	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-89e4df10d3690e5a6d15	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0900000000-89e4df10d3690e5a6d15	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27616

Phenol-Explorer ID

718

DrugBank ID

Not Available

HMDB ID

HMDB34272

CRC / DFC (Dictionary of Food Compounds) ID

HJG27-Y:HJG27-Y

EAFUS ID

Not Available

Dr. Duke ID

FICUSIN|PSORALEN

BIGG ID

Not Available

KNApSAcK ID

C00000297

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

Psoralen

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti leukodermic			DUKE
anti mitotic			DUKE
anti mutagenic			DUKE
anti psoriac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE

Showing 1 to 10 of 28 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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Psoralen (FDB012605)

Structure for FDB012605 (Psoralen)