IMPPAT Phytochemical information: 
Besigomsin
Besigomsin
Summary

SMILES: COc1cc2C[C@](C)(O)[C@@H](C)Cc3c(-c2c(c1OC)OC)c(OC)c1c(c3)OCO1
InChI: InChI=1S/C23H28O7/c1-12-7-13-8-16-20(30-11-29-16)22(28-6)17(13)18-14(10-23(12,2)24)9-15(25-3)19(26-4)21(18)27-5/h8-9,12,24H,7,10-11H2,1-6H3/t12-,23-/m0/s1
InChIKey: ZWRRJEICIPUPHZ-MYODQAERSA-N
DeepSMILES: COcccC[C@]C)O)[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: cOC; CO; c1cOCO1
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:
gomisin a, Wuweizichun B, wuweizichun b, Gomisin A
External chemical identifiers:
CID:CID_3001662; ChEMBL:CHEMBL403578; ZINC:ZINC000004212127; FDASRS:L5U70J87J8; SureChEMBL:SCHEMBL712401; MolPort-006-668-420
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Besigomsin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 416.47
Log P RDKit 3.6
Topological polar surface area (Å2) RDKit 75.61
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 4
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
Besigomsin
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 0.816107
Besigomsin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.07
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Besigomsin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000311032CASP3800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.