IMPPAT Phytochemical information: 
Psoralenol

Psoralenol
Summary

SMILES: Oc1ccc2c(c1)occ(c2=O)c1ccc2c(c1)CC(C(O2)(C)C)O
InChI: InChI=1S/C20H18O5/c1-20(2)18(22)8-12-7-11(3-6-16(12)25-20)15-10-24-17-9-13(21)4-5-14(17)19(15)23/h3-7,9-10,18,21-22H,8H2,1-2H3
InChIKey: IPXXMSXJVCGTCG-UHFFFAOYSA-N
DeepSMILES: Occcccc6)occc6=O))cccccc6)CCCO6)C)C))O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccc3c(c2)CCCO3)coc2ccccc12
Scaffold Graph/Node level: OC1C(C2CCC3OCCCC3C2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCC2CCCCC2C1
Functional groups: cO; coc; c=O; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Pyranoisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
Psoralenol, psoralenol
External chemical identifiers:
CID:CID_5320772
Chemical structure download


Psoralenol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.36
Log P RDKit 3.24
Topological polar surface area (Å2) RDKit 79.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
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 1
Stereochemical complexity RDKit 0.05
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 1
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Psoralenol
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 0.71


Psoralenol
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.35
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes