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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:49:40 UTC
Update Date2019-07-23 06:15:01 UTC
HMDB IDHMDB0034050
Secondary Accession Numbers
  • HMDB34050
Metabolite Identification
Common NamePsoralidin
DescriptionPsoralidin belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, psoralidin is considered to be a flavonoid lipid molecule. It has the capability to inhibit protein tyrosine phosphatase 1B, a key metabolite involved in insulin signaling. To form the ring of psoralidin, an intramolecular cyclization occurs, finished off by a microwave assisted cross metathesis reaction. Structurally, psoralidin is a coumestan derivative; it has an isopentenyl group at the second carbon position of coumestrol. Psoralidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Psoralidin has been detected, but not quantified in, a few different foods, such as fruits, lima beans, and pulses. This could make psoralidin a potential biomarker for the consumption of these foods. Psoralidin is a natural phenolic compound found in the seeds of Psoralea corylifolia. Dopamine levels changed as well as a result of psoralidin consumption. Psoralidin raised 5-hydroxytryptamine and 5-hydroxyindoleacetic acid levels in the brain. Recently, it has shown activity in vitro against gastric, colon, prostate, and breast cancer lines. Psoralidin production starts with a based catalyzed condensation between phenyl acetate and acid chloride.
Structure
Data?1563862501
Synonyms
ValueSource
3,9-Dihydroxy-2-prenylcoumestanChEBI
Chemical FormulaC20H16O5
Average Molecular Weight336.338
Monoisotopic Molecular Weight336.099773622
IUPAC Name5,14-dihydroxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
Traditional Namepsoralidin
CAS Registry Number18642-23-4
SMILES
CC(C)=CCC1=CC2=C(OC(=O)C3=C2OC2=C3C=CC(O)=C2)C=C1O
InChI Identifier
InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3
InChI KeyYABIJLLNNFURIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 - 292 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.064 g/LALOGPS
logP4.63ALOGPS
logP4.13ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.92ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.86 m³·mol⁻¹ChemAxon
Polarizability36.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-3649000000-fb4bed2219264a94b2c0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06di-2021900000-af5a7fcfd2abc930bab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0029000000-611c9c21982e8c8417bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-5097000000-522ed689eb20e83a6060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-9160000000-7eabc2db1056ba50d5b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-7390a95ac6006bbd4672Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0039000000-6317b2200c19c15fe546Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-2892000000-2dc8e8c23fe68b07d783Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
FooDB IDFDB012294
KNApSAcK IDC00002566
Chemspider ID4445118
KEGG Compound IDC10523
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPsoralidin
METLIN IDNot Available
PubChem Compound5281806
PDB IDNot Available
ChEBI ID8616
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .