IMPPAT Phytochemical information: 
Squamosamide
Squamosamide
Summary

SMILES: COc1cc(cc(c1O)OC)/C(=C\c1ccc(c(c1)OC)O)/C(=O)NCCc1ccc(cc1)O
InChI: InChI=1S/C26H27NO7/c1-32-22-13-17(6-9-21(22)29)12-20(18-14-23(33-2)25(30)24(15-18)34-3)26(31)27-11-10-16-4-7-19(28)8-5-16/h4-9,12-15,28-30H,10-11H2,1-3H3,(H,27,31)/b20-12+
InChIKey: VEUGFVRUMOLGFJ-UDWIEESQSA-N
DeepSMILES: COcccccc6O))OC))))/C=C\cccccc6)OC)))O))))))/C=O)NCCcccccc6))O
Scaffold Graph/Node/Bond level: O=C(NCCc1ccccc1)C(=Cc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(NCCC1CCCCC1)C(CC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)C(CC1CCCCC1)C1CCCCC1
Functional groups: cOC; cO; c/C=C(\c)C(=O)NC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acid amides
Synonymous chemical names:
squamosamide, Squamosamide
External chemical identifiers:
CID:CID_5321487; ChEMBL:CHEMBL4129283
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Squamosamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 465.5
Log P RDKit 3.73
Topological polar surface area (Å2) RDKit 117.48
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
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 21
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3
Squamosamide
Drug-likeness
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 0.280971
Squamosamide
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 -6.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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