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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:36 UTC
Update Date2019-01-11 19:48:11 UTC
HMDB IDHMDB0034272
Secondary Accession Numbers
  • HMDB34272
Metabolite Identification
Common NamePsoralen
DescriptionPsoralen 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
Structure
Data?1547236091
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
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]Chromen-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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pbi-0900000000-f4158c6b7c0ecf20d9feJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0r2i-6900000000-276c6db470fc13777449JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pbi-0900000000-f4158c6b7c0ecf20d9feJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0r2i-6900000000-276c6db470fc13777449JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-1900000000-900e13490ddfba7e89efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-ac91ad62c36a29665a71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-75211365e04f08273288JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-fa9d08e8d5421ebeaa77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f89-0900000000-bacd49139ec536fb55e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-ac91ad62c36a29665a71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-0900000000-195d9e7e3b29cf95c327JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-287480067e742345fcb9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-2bf4a5ffe9d6883b015eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-519db61c8cb6a8a31549JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-559cba64d14574cb0041JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-503a6a3d5ba551e5c0f5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-857f114f045cf9aa2b39JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-052r-3900000000-eff7b2146482de5c7740JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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
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
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.. .