ContaminantDB: Psoralen

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-06-08 16:35:18 UTC

Update Date

2026-05-14 20:08:58 UTC

Accession Number

CHEM000731

Identification

Common Name

Psoralen

Class

Small Molecule

Description

Psoralen is found in carrot. Psoralen is found in common vegetables, e.g. parsnip, celery especially if diseased or `spoiled' Psoralen is a significant mutagen and is used for this purpose in molecular biology research. Psoralen has been shown to exhibit anti-proliferative, anti-allergenic and anti-histamine functions (1, 2, 2). Psoralen belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Aromatic Hydrocarbon
Ester
Food Toxin
Furocoumarin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid delta-lactone	ChEBI
6,7-Furanocoumarin	ChEBI
6-Hydroxy-5-benzofuranacrylic acid delta-lactone	ChEBI
7H-Furo[3,2-g][1]benzopyran-7-one	ChEBI
Ficusin	ChEBI
Furo[2',3':7,6]coumarin	ChEBI
Furo[4',5':6,7]coumarin	ChEBI
Furocoumarin	ChEBI
Manaderm	ChEBI
Psoralene	ChEBI
7H-Furo[3,2-g]chromen-7-one	Kegg
3-(6-Hydroxy-5-benzofuranyl)-2-propenoate delta-lactone	Generator
3-(6-Hydroxy-5-benzofuranyl)-2-propenoate δ-lactone	Generator
3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid δ-lactone	Generator
6-Hydroxy-5-benzofuranacrylate delta-lactone	Generator
6-Hydroxy-5-benzofuranacrylate δ-lactone	Generator
6-Hydroxy-5-benzofuranacrylic acid δ-lactone	Generator
2H-furo[3,2-g]Chromen-2-one	HMDB
5-Benzofuranacrylic acid, 6-hydroxy-, delta-lactone	HMDB
6-Hydroxy-5-benzofuranacrylic acid beta-lactone	HMDB
6-Hydroxy-5-benzofuranacrylic acid gamma-lactone	HMDB
7H-furo(3,2-g)(1)Benzopyran-7-one	HMDB
7H-furo[3,2-g]Benzopyran-7-one	HMDB
7H-furo[3,2-g][1]Benzopyran-7-one, 9ci	HMDB
furo(2',3',7,6)Coumarin	HMDB
furo(3,2-g)-Coumarin	HMDB
furo(4',5',6,7)Coumarin	HMDB
furo[2'.3':7.6]Coumarin	HMDB
furo[3,2-g]Coumarin	HMDB
Phytoalexin	HMDB
Phytoalexin-CMPD	HMDB
Psorline-P	HMDB

Chemical Formula

C₁₁H₆O₃

Average Molecular Mass

186.166 g/mol

Monoisotopic Mass

186.032 g/mol

CAS Registry Number

66-97-7

IUPAC Name

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

Traditional Name

psoralen

SMILES

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

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

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.

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

plant metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	171°C
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0pbi-0900000000-f4158c6b7c0ecf20d9fe	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0r2i-6900000000-276c6db470fc13777449	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0pbi-0900000000-f4158c6b7c0ecf20d9fe	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0r2i-6900000000-276c6db470fc13777449	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052u-1900000000-900e13490ddfba7e89ef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00lr-1900000000-ac91ad62c36a29665a71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-75211365e04f08273288	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00lr-0900000000-fa9d08e8d5421ebeaa77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0f89-0900000000-bacd49139ec536fb55e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-1900000000-ac91ad62c36a29665a71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001r-0900000000-195d9e7e3b29cf95c327	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-75211365e04f08273288	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0900000000-fa9d08e8d5421ebeaa77	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-0900000000-bacd49139ec536fb55e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-287480067e742345fcb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-2bf4a5ffe9d6883b015e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-1900000000-519db61c8cb6a8a31549	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-559cba64d14574cb0041	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-503a6a3d5ba551e5c0f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-857f114f045cf9aa2b39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-f3f07adc83a68e9e76ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f3f07adc83a68e9e76ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-a2c2c14d0cf6b23ada92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-89e4df10d3690e5a6d15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-89e4df10d3690e5a6d15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0900000000-89e4df10d3690e5a6d15	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052r-3900000000-eff7b2146482de5c7740	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (7).

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (6)

Uses/Sources

Anthelmintics, cross-linking reagent, photosensitising agent. Photochemical reagent for the investigation of nucleic acid structure and function. (7)

Minimum Risk Level

Not Available

Health Effects

The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (6). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (3). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (8) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs.

Symptoms

Harmful if swallowed. Irritating to eyes, respiratory system and skin. (7)

Treatment

In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. (7)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034272

FooDB ID