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Record Information
Version1.0
Created at2012-09-11 19:04:36 UTC
Updated at2024-05-11 00:24:50 UTC
NP-MRD IDNP0000003
Secondary Accession NumbersNone
Natural Product Identification
Common NamePsoralen
DescriptionPsoralen, also known as psoralene, 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 the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. Psoralen is structurally related to coumarin by the addition of a fused furan ring and is considered as a derivative of umbelliferone. Biosynthetically, psoralen originates from coumarins in the shikimate pathway. Psoralen is produced exclusively by plants but can be found in animals that consume these plants. Psoralen can be found in several plant sources with Ficus carica (the common fig) being probably the most abundant source of psoralens. They are also found in small quantities in Ammi visnaga (bisnaga), Pastinaca sativa (parsnip), Petroselinum crispum (parsley), Levisticum officinale (lovage), Foeniculum vulgare (fruit, i.E., Fennel seeds), Daucus carota (carrot), Psoralea corylifolia (babchi), Apium graveolens (celery), and bergamot oil (bergapten, bergamottin). Psoralen is found in all citrus fruits. Psoralen is a well-known mutagen and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent inter-strand cross-links (ICL) with thymines in the DNA molecule. Psoralen also functions as a drug. An important use of psoralen is in the treatment for skin problems such as psoriasis and, to a lesser extent, eczema and vitiligo. This treatment takes advantage of the high UV absorbance of psoralen. In treating these skin conditions psoralen is applied first to sensitise the skin, then UVA light is applied to clean up the skin problem. Psoralen has also been recommended for treating alopecia.
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 Mass186.1660 Da
Monoisotopic Mass186.03169 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number66-97-7
SMILESNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2024-05-09View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CDCl3, simulated)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2024-05-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Aegle marmelosPlant
Aloe veraPlant
Ammi majusPlant
Angelica archangelica
Angelica dahurica
Angelica japonica
Angelica keiskei
Angelica lucida
Angelica pubescens
Angelica pubescens f.biserrataPlant
Angelica shikokiana
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Jian Tang, Yuangang Zhang, Thomas G. Hartman, Robert T. Rosen, and Chi Tang Ho. Free and glycosid...
Arabidopsis thalianaPlant
Arracacia xanthorrhizaPlant
Bituminaria bituminosaPlant
Brosimum acutifolium
Brosimum gaudichaudii
Bupleurum scorzonerifoliumPlant
Citrus aurantiifolia
Citrus bergamiaPlant
Citrus medica
Coriandrum sativum L.FooDB
Coronilla coronataPlant
Coronilla glaucaPlant
Coronilla junceaPlant
Coronilla minimaPlant
Coronilla repandaPlant
Coronilla scorpioidesPlant
Coronilla vaginalis
Coronilla valentinaPlant
Coronilla viminalisPlant
Cryptocarya obovata
Cullen corylifoliumPlant
Cullen drupaceumPlant
Cullen lachnostachys
Cullen obtusifoliumPlant
Cullen plicatumPlant
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dictamnus albus
Dictamnus dasycarpus
Dictamnus hispanicusPlant
Diplotaenia damavandica
Dorstenia asaroidesPlant
Dorstenia bahiensisPlant
Dorstenia barnimianaPlant
Dorstenia brasiliensisPlant
Dorstenia bryonifoliaPlant
Dorstenia cayapiaaPlant
Dorstenia contrajervaPlant
Dorstenia drakenaPlant
Dorstenia elliptica
Dorstenia excentriaPlant
Dorstenia excentrica
Dorstenia foetida
Dorstenia heringeriiPlant
Dorstenia lindenianaPlant
Dorstenia prorepens
Dorstenia psilurusPlant
Dorstenia turbinataPlant
Erycibe expansaPlant
Erythroxylum uleiPlant
Fagara mayuPlant
Fatoua villosa
Feijoa sellowianaPlant
Feroniella lucida
Ficus aricaPlant
Ficus caricaFooDB
Ficus erecta
Ficus hirtaPlant
Ficus pumila
Ficus simplicissimaPlant
Ficus sycomorusPlant
Foeniculum vulgareFooDB
Glehnia littoralisPlant
Haplophyllum patavinumPlant
Heracleum grandiflorum
Heracleum lanatumPlant
Heracleum lehmannianum
Heracleum leskovii
Heracleum levskoviiPlant
Heracleum mantegazzianum
Heracleum persicum
Hoita macrostachyaPlant
Leionema ambiens
Levisticum officinaleFooDB
Limonia acidissimaPlant
Melicope barbigera
Melicope borbonica
Mitracarpus hirtus
Orbexilum pedunculatumPlant
Otholobium bolusiiPlant
Otholobium candicansPlant
Otholobium foliosumPlant
Otholobium glandulosum
Otholobium hirtumPlant
Otholobium obliquumPlant
Otholobium parviflorumPlant
Otholobium sericeumPlant
Otholobium stachyerumPlant
Otholobium zeyheriPlant
Pastinaca sativaFooDB
Pediomelum canescens
Pediomelum subacaulePlant
Petroselinum crispumFooDB
Peucedanum japonicum
Peucedanum praeruptorumPlant
Phebalium argenteumPlant
Phebalium clavatumPlant
Plumbago zeylanicaPlant
Prangos lipskyi
Prangos tschimganica
Prionosciadium thapsoidesPlant
Psoralea affinisPlant
Psoralea arboreaPlant
Psoralea cinereaPlant
Psoralea coryfoliaPlant
Psoralea effusaPlant
Psoralea exilePlant
Psoralea fascicularisPlant
Psoralea glabraPlant
Psoralea lachnostachysPlant
Psoralea leucanthaPlant
Psoralea martiniiPlant
Psoralea onobrychis
Psoralea oreopolumPlant
Psoralea papillosaPlant
Psoralea pinnataPlant
Psoralea plumosaPlant
Psoralea pullataPlant
Psoralea pustulataPlant
Psoralea ramulosaPlant
Psoralea repensPlant
Psoralea speciosaPlant
Psoralea verrucosaPlant
Rhadinothamnus anceps
Rhadinothamnus rudis
Ruta chalepensisPlant
Ruta corsica
Ruta graveolensPlant
Saposhnikovia divaricata
Saposhnikovia divaricata SchischkinPlant
Sarcolobus globosus-
Securigera creticaPlant
Securigera orientalisPlant
Skimmia laureola
Taxus chinensisPlant
Thamnosma texana
Tithonia diversifolia
Trichocline caulescens
tuberosa
      Not Available
Zanthoxylum americanum
Zanthoxylum beecheyanum
Zanthoxylum flavumPlant
Zanthoxylum mayu
Zanthoxylum zanthoxyloides
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
LogP4.02Not Available
Predicted PropertiesNot 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
Good Scents IDNot Available
References
General References
  1. Rodighiero P, Guiotto A, Pastorini G, Manzini P, Bordin F, Baccichetti F, Carlassare F, Vedaldi D, Dall'Acqua F: Photochemical and photobiological properties of 4,5'-dimethylpsoralen, a bifunctional contaminant of synthetic 4,5'-dimethylangelicin. Farmaco Sci. 1981 Jul;36(7):648-62. [PubMed:7274446 ]
  2. Insawang M, Wongpraparut C: Recalcitrant solar urticaria induced by UVA and visible light: a case report. J Med Assoc Thai. 2010 Oct;93(10):1238-41. [PubMed:20973330 ]
  3. 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 ]
  4. Wong RW, Rabie AB: Effect of psoralen on bone formation. J Orthop Res. 2011 Feb;29(2):158-64. doi: 10.1002/jor.21124. [PubMed:20196083 ]
  5. Lee SJ, Nam KW, Mar W: Effects of psoralen from Psoralea corylifolia on quinone reductase, ornithine decarboxylase, and JB6 cells transformation promotion. Arch Pharm Res. 2011 Jan;34(1):31-6. doi: 10.1007/s12272-011-0103-6. Epub 2011 Apr 6. [PubMed:21468912 ]
  1. He RS, Li SW, Yang TT, Lai JX, Liu XJ, Xue BX, Zhang LH, Wu HH: Furfural Derivatives and Phenolic Constituents in Stemona tuberosa Lour. Chem Biodivers. 2023 Sep;20(9):e202300693. doi: 10.1002/cbdv.202300693. Epub 2023 Sep 6. [PubMed:37614210 ]