IMPPAT Phytochemical information: 
Rubschisantherin

Rubschisantherin
Summary

SMILES: COc1cc2[C@H](OC(=O)C)[C@@H](C)[C@@H](C)Cc3c(-c2c(c1OC)OC)c(OC)c1c(c3)OCO1
InChI: InChI=1S/C25H30O8/c1-12-8-15-9-18-23(32-11-31-18)24(29-6)19(15)20-16(21(13(12)2)33-14(3)26)10-17(27-4)22(28-5)25(20)30-7/h9-10,12-13,21H,8,11H2,1-7H3/t12-,13-,21+/m0/s1
InChIKey: GRHNKVUUWRVFMM-OYMPBJRDSA-N
DeepSMILES: COccc[C@H]OC=O)C)))[C@@H]C)[C@@H]C)Ccc-c8cc%12OC)))OC))))cOC))ccc6)OCO5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCCCc1cc3c(cc1-2)OCO3
Scaffold Graph/Node level: C1CCC2CC3OCOC3CC2C2CCCCC2C1
Scaffold Graph level: C1CC2CC3CCCCC4CCCCC4C3CC2C1
Functional groups: CC(=O)OC; c1cOCO1; cOC
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:
rubschisantherin
External chemical identifiers:
CID:73353444; ChEMBL:CHEMBL2386335; ZINC:ZINC000015262542
Chemical structure download


Rubschisantherin
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


Rubschisantherin
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 0.6039


Rubschisantherin
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 0.0
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