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Record Information
Version2.0
Created at2012-09-11 19:04:36 UTC
Updated at2025-02-11 15:45:11 UTC
NP-MRD IDNP0000003
Natural Product DOIhttps://doi.org/10.57994/0875
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
Chemical FormulaC11H6O3
Average Mass186.1660 Da
Monoisotopic Mass186.03169 Da
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
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
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
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
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 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
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. 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 ]
  4. 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 ]
  5. 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 ]
  6. DOI: 10.1002/cbdv.202300693