IMPPAT Phytochemical information: 
Pisatin

Pisatin
Summary

SMILES: COc1ccc2c(c1)OC[C@]1([C@@H]2Oc2c1cc1c(c2)OCO1)O
InChI: InChI=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/t16-,17+/m1/s1
InChIKey: LZMRDTLRSDRUSU-SJORKVTESA-N
DeepSMILES: COcccccc6)OC[C@][C@@H]6Occ5cccc6)OCO5))))))))))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)OCC1c3cc4c(cc3OC21)OCO4
Scaffold Graph/Node level: C1CCC2C(C1)OCC1C3CC4OCOC4CC3OC21
Scaffold Graph level: C1CC2CC3CC4C5CCCCC5CCC4C3CC2C1
Functional groups: cOC; c1cOCO1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Furanoisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Pterocarpan
Synonymous chemical names:
(+)-pisatin, Pisatin, pisatin
External chemical identifiers:
CID:CID_101689; ChEMBL:CHEMBL1784262; ChEBI:CHEBI:67347; ZINC:ZINC000001531872; FDASRS:V6L86DZ4N3; MolPort-019-937-214
Chemical structure download


Pisatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 314.29
Log P RDKit 2.14
Topological polar surface area (Å2) RDKit 66.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Pisatin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.87


Pisatin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No