IMPPAT Phytochemical information: 
Scirpusin B

Scirpusin B
Summary

SMILES: Oc1cc(/C=C/c2ccc(c(c2)O)O)c2c(c1)OC(C2c1cc(O)cc(c1)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C28H22O8/c29-18-9-17(10-19(30)12-18)27-26-15(3-1-14-2-5-21(32)23(34)7-14)8-20(31)13-25(26)36-28(27)16-4-6-22(33)24(35)11-16/h1-13,27-35H/b3-1+
InChIKey: MTYSFTYBAMMIGE-HNQUOIGGSA-N
DeepSMILES: Occc/C=C/cccccc6)O))O)))))))ccc6)OCC5cccO)ccc6)O)))))))cccccc6)O))O
Scaffold Graph/Node/Bond level: C(=Cc1cccc2c1C(c1ccccc1)C(c1ccccc1)O2)c1ccccc1
Scaffold Graph/Node level: C1CCC(CCC2CCCC3OC(C4CCCCC4)C(C4CCCCC4)C23)CC1
Scaffold Graph level: C1CCC(CCC2CCCC3CC(C4CCCCC4)C(C4CCCCC4)C23)CC1
Functional groups: cO; c/C=C/c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Stilbenoids
NP Classifier Class: Oligomeric stibenes
Synonymous chemical names:
scirpusin b
External chemical identifiers:
CID:CID_5458999; ChEMBL:CHEMBL514088; SureChEMBL:SCHEMBL15440888
Chemical structure download


Scirpusin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 486.48
Log P RDKit 5.06
Topological polar surface area (Å2) RDKit 150.84
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 26
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
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


Scirpusin B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.156179


Scirpusin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.94
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No