IMPPAT Phytochemical information: 
Diphyllin

Diphyllin
Summary

SMILES: COc1cc2c(c3ccc4c(c3)OCO4)c3C(=O)OCc3c(c2cc1OC)O
InChI: InChI=1S/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3
InChIKey: VMEJANRODATDOF-UHFFFAOYSA-N
DeepSMILES: COcccccccccc6)OCO5))))))))cC=O)OCc5cc9cc%13OC)))))O
Scaffold Graph/Node/Bond level: O=C1OCc2cc3ccccc3c(-c3ccc4c(c3)OCO4)c21
Scaffold Graph/Node level: OC1OCC2CC3CCCCC3C(C3CCC4OCOC4C3)C21
Scaffold Graph level: CC1CCC2CC3CCCCC3C(C3CCC4CCCC4C3)C12
Functional groups: cOC; c1cOCO1; cC(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Arylnaphthalene lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
diphyllin
External chemical identifiers:
CID:CID_100492; ChEMBL:CHEMBL221190; ChEBI:CHEBI:4645; ZINC:ZINC000000828203; FDASRS:W4PN5LDP26; SureChEMBL:SCHEMBL1061765; MolPort-001-933-059
Chemical structure download


Diphyllin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.35
Log P RDKit 3.63
Topological polar surface area (Å2) RDKit 83.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
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 17
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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


Diphyllin
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 0.694847


Diphyllin
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 -6.05
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Diphyllin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000285393ATP6V0D2786
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.