IMPPAT Phytochemical information: 
Isopsoralidin

Isopsoralidin
Summary

SMILES: Oc1ccc2c(c1)oc1c2c(=O)oc2c1cc1CCC(Oc1c2)(C)C
InChI: InChI=1S/C20H16O5/c1-20(2)6-5-10-7-13-16(9-14(10)25-20)24-19(22)17-12-4-3-11(21)8-15(12)23-18(13)17/h3-4,7-9,21H,5-6H2,1-2H3
InChIKey: JWCDJOWFOVBBCP-UHFFFAOYSA-N
DeepSMILES: Occcccc6)occ5c=O)occ6ccCCCOc6c%10)))C)C
Scaffold Graph/Node/Bond level: O=c1oc2cc3c(cc2c2oc4ccccc4c12)CCCO3
Scaffold Graph/Node level: OC1OC2CC3OCCCC3CC2C2OC3CCCCC3C12
Scaffold Graph level: CC1CC2CC3CCCCC3CC2C2CC3CCCCC3C12
Functional groups: cO; coc; c=O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Coumestans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Coumestan
Synonymous chemical names:
isopsoralidin
External chemical identifiers:
CID:CID_12304285; ZINC:ZINC000013408699
Chemical structure download


Isopsoralidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.34
Log P RDKit 4.5
Topological polar surface area (Å2) RDKit 72.81
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
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


Isopsoralidin
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.48


Isopsoralidin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.44
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes