Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2019-11-26 03:05:35 UTC
Primary IDFDB011855
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePisatin
DescriptionPisatin belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Pisatin is an extremely weak basic (essentially neutral) compound (based on its pKa). Pisatin has been detected, but not quantified in, several different foods, such as common pea, herbs and spices, pulses, and tea. This could make pisatin a potential biomarker for the consumption of these foods.
CAS Number469-01-2
Structure
Thumb
Synonyms
SynonymSource
(+)-PisatinHMDB
6a-Hydroxy-3-methoxy-8,9-methylenedioxypterocarpanHMDB
(S,S)-PisatinMeSH
Pisatin, (6as-cis)-isomerMeSH
Pisatin, (6ar-cis)-isomerMeSH
PisatinMeSH
(-)-PisatinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP1.75ALOGPS
logP1.78ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.98ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.94 m³·mol⁻¹ChemAxon
Polarizability31.73 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H14O6
IUPAC name16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-1-ol
InChI IdentifierInChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3
InChI KeyLZMRDTLRSDRUSU-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C2C3OC4=C(C=C5OCOC5=C4)C3(O)COC2=C1
Average Molecular Weight314.2895
Monoisotopic Molecular Weight314.07903818
Classification
Description belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Isoflavanol
  • Pterocarpan
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Benzofuran
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Oxacycle
  • Ether
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.97%; H 4.49%; O 30.54%DFC
Melting PointMp 61°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.58ARNOLDI,A & MERLINI,L (1990)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +280 (c, 0.11 in EtOH)DFC
Spectroscopic UV Data309 (e 7250) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06sa-1691000000-274d0a6517fe3252562bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9328000000-e689e98a16aeffb2e091JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-51ff895d3d542958b762JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0039000000-0352732548637eab03f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-7930000000-ac982921a96b24070af6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-226bc1be39e0a6889bbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0039000000-32e07322e048d0dfd736JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr2-1090000000-82ba48e1b539fc3da501JSpectraViewer
ChemSpider ID3682780
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID4484953
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33732
CRC / DFC (Dictionary of Food Compounds) IDGZS70-L:HBB41-V
EAFUS IDNot Available
Dr. Duke IDPISATIN
BIGG IDNot Available
KNApSAcK IDC00000651
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.