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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:36 UTC
Update Date2019-07-23 06:15:38 UTC
HMDB IDHMDB0034272
Secondary Accession Numbers
  • HMDB34272
Metabolite 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. Classically, two chambers of psoralen and buffered DNA solution are partitioned by a semi-permeable membrane; the affinity of the psoralen for DNA is directly related to the concentration of the psoralen in the DNA chamber after equilibrium. 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 in a few different foods, such as figs, parsley, and parsnips and in a lower concentration in lovages, wild carrots, and celery stalks. psoralen has also been detected, but not quantified in, several different foods, such as hard wheats, greenthread tea, kiwis, narrowleaf cattails, and sweet rowanberries. This could make psoralen a potential biomarker for the consumption of these foods. Psoralen is a potentially toxic compound.
Structure
Data?1563862538
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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.67Not 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pbi-0900000000-f4158c6b7c0ecf20d9feSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0r2i-6900000000-276c6db470fc13777449Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pbi-0900000000-f4158c6b7c0ecf20d9feSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0r2i-6900000000-276c6db470fc13777449Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-1900000000-900e13490ddfba7e89efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-ac91ad62c36a29665a71Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-75211365e04f08273288Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-fa9d08e8d5421ebeaa77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f89-0900000000-bacd49139ec536fb55e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-ac91ad62c36a29665a71Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-0900000000-195d9e7e3b29cf95c327Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-287480067e742345fcb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-2bf4a5ffe9d6883b015eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-519db61c8cb6a8a31549Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-559cba64d14574cb0041Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-503a6a3d5ba551e5c0f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-857f114f045cf9aa2b39Spectrum
MSMass Spectrum (Electron Ionization)splash10-052r-3900000000-eff7b2146482de5c7740Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID718
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .