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Record Information
Version1.0
Created at2012-09-11 19:04:36 UTC
Updated at2020-09-11 01:32:46 UTC
NP-MRD IDNP0000003
Secondary Accession NumbersNone
Natural Product Identification
Common NamePsoralen
DescriptionPsoralen, 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. 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. All photobiological effects of furocoumarins result from their photochemical reactions. Psoralen is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Psoralen is found, on average, in the highest concentration within a few different foods, such as figs, parsley, and parsnips and in a lower concentration in lovages, carrots, and wild carrots. Psoralen has also been detected, but not quantified in, several different foods, such as radish (var.), Elliott's blueberries, squashberries, pepper (c. Annuum), and gram beans. This could make psoralen a potential biomarker for the consumption of these foods. Psoralen is a potentially toxic compound. Psoralen is a significant mutagen and is used for this purpose in molecular biology research. 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). 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. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. The Psoralen 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135).
Structure
Thumb
Synonyms
ValueSource
3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid delta-lactoneChEBI
6,7-FuranocoumarinChEBI
6-Hydroxy-5-benzofuranacrylic acid delta-lactoneChEBI
7H-Furo[3,2-g][1]benzopyran-7-oneChEBI
FicusinChEBI
Furo[2',3':7,6]coumarinChEBI
Furo[4',5':6,7]coumarinChEBI
FurocoumarinChEBI
ManadermChEBI
PsoraleneChEBI
7H-Furo[3,2-g]chromen-7-oneKegg
3-(6-Hydroxy-5-benzofuranyl)-2-propenoate delta-lactoneGenerator
3-(6-Hydroxy-5-benzofuranyl)-2-propenoate δ-lactoneGenerator
3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid δ-lactoneGenerator
6-Hydroxy-5-benzofuranacrylate delta-lactoneGenerator
6-Hydroxy-5-benzofuranacrylate δ-lactoneGenerator
6-Hydroxy-5-benzofuranacrylic acid δ-lactoneGenerator
2H-Furo[3,2-g]chromen-2-oneHMDB
5-Benzofuranacrylic acid, 6-hydroxy-, delta-lactoneHMDB
6-Hydroxy-5-benzofuranacrylic acid beta-lactoneHMDB
6-Hydroxy-5-benzofuranacrylic acid gamma-lactoneHMDB
7H-Furo(3,2-g)(1)benzopyran-7-oneHMDB
7H-Furo[3,2-g]benzopyran-7-oneHMDB
7H-Furo[3,2-g][1]benzopyran-7-one, 9ciHMDB
Furo(2',3',7,6)coumarinHMDB
Furo(3,2-g)-coumarinHMDB
Furo(4',5',6,7)coumarinHMDB
Furo[2'.3':7.6]coumarinHMDB
Furo[3,2-g]coumarinHMDB
PhytoalexinHMDB
Phytoalexin-CMPDHMDB
Psorline-pHMDB
Chemical FormulaC11H6O3
Average Molecular Weight186.166
Monoisotopic Molecular Weight186.031694053
IUPAC Name7H-furo[3,2-g]chromen-7-one
Traditional Namepsoralen
CAS Registry Number66-97-7
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 KeyZCCUUQDIBDJBTK-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Plantae
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 - 115 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.51 g/LNot Available
LogP4.02MCFARLAND,JW ET AL. (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.15ALOGPS
logP1.94ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.39 m³·mol⁻¹ChemAxon
Polarizability18.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0034272
DrugBank IDNot Available
Phenol Explorer Compound ID718
FoodDB IDFDB012605
KNApSAcK IDC00000297
Chemspider ID5964
KEGG Compound IDC09305
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPsoralen
METLIN IDNot Available
PubChem Compound6199
PDB IDNot Available
ChEBI ID27616
References
General References
  1. Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [PubMed:17051490 ]