IMPPAT Phytochemical information: 
Isopimpinellin

Isopimpinellin
Summary

SMILES: COc1c2ccc(=O)oc2c(c2c1cco2)OC
InChI: InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
InChIKey: DFMAXQKDIGCMTL-UHFFFAOYSA-N
DeepSMILES: COccccc=O)oc6ccc%10cco5)))))OC
Scaffold Graph/Node/Bond level: O=c1ccc2cc3ccoc3cc2o1
Scaffold Graph/Node level: OC1CCC2CC3CCOC3CC2O1
Scaffold Graph level: CC1CCC2CC3CCCC3CC2C1
Functional groups: cOC; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Furanocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins
Synonymous chemical names:
isopimpinellin (5,8-dimethoxy psoralen), isopimpinellin, Isopimpinellin
External chemical identifiers:
CID:CID_68079; ChEMBL:CHEMBL140796; ChEBI:CHEBI:28853; ZINC:ZINC000000314951; FDASRS:20GCF755G6; SureChEMBL:SCHEMBL498907; MolPort-000-882-064
Chemical structure download


Isopimpinellin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 246.22
Log P RDKit 2.56
Topological polar surface area (Å2) RDKit 61.81
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 18
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 11
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


Isopimpinellin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.650084


Isopimpinellin
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 -6.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Isopimpinellin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000260630CYP1B1700
ENSP00000336528NR1I2700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.