IMPPAT Phytochemical information: 
Kadsurin

Kadsurin
Summary

SMILES: COc1cc2C[C@@H](C)[C@@H](C)[C@H](c3c(-c2c(c1OC)OC)c(OC)c1c(c3)OCO1)OC(=O)C
InChI: InChI=1S/C25H30O8/c1-12-8-15-9-17(27-4)22(28-5)24(29-6)19(15)20-16(21(13(12)2)33-14(3)26)10-18-23(25(20)30-7)32-11-31-18/h9-10,12-13,21H,8,11H2,1-7H3/t12-,13-,21-/m1/s1
InChIKey: QUGMSTJBNZWXQS-SQHYZVFZSA-N
DeepSMILES: COcccC[C@@H]C)[C@@H]C)[C@H]cc-c8cc%12OC)))OC))))cOC))ccc6)OCO5))))))))OC=O)C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCCCc1cc3c(cc1-2)OCO3
Scaffold Graph/Node level: C1CCC2CC3OCOC3CC2C2CCCCC2C1
Scaffold Graph level: C1CC2CC3CCCCC4CCCCC4C3CC2C1
Functional groups: cOC; c1cOCO1; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzocyclooctadienes lignans
Synonymous chemical names:
kadsurin
External chemical identifiers:
CID:CID_171064; ChEMBL:CHEMBL559796; ChEBI:CHEBI:67453; ZINC:ZINC000015270773; MolPort-044-754-143
Chemical structure download


Kadsurin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 458.51
Log P RDKit 4.55
Topological polar surface area (Å2) RDKit 81.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Kadsurin
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.603932


Kadsurin
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 -5.84
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No