IMPPAT Phytochemical information: 
Squarrosin
Squarrosin
Summary

SMILES: COc1cc(ccc1OC)c1coc2c(c1=O)c(O)c1c(c2)OCO1
InChI: InChI=1S/C18H14O7/c1-21-11-4-3-9(5-12(11)22-2)10-7-23-13-6-14-18(25-8-24-14)17(20)15(13)16(10)19/h3-7,20H,8H2,1-2H3
InChIKey: ZXWGLCIRUZGYPA-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC)))))ccoccc6=O))cO)ccc6)OCO5
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2cc3c(cc12)OCO3
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CC3OCOC3CC21
Scaffold Graph level: CC1C(C2CCCCC2)CCC2CC3CCCC3CC21
Functional groups: cOC; coc; c=O; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: O-methylated isoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
squarrosin, Squarrosin, squarrosin [5-hydroxy-3',4'-dimethoxy-6,7-methylenedioxyisoflavone]
External chemical identifiers:
CID:CID_14507160; ZINC:ZINC000014646059
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Squarrosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.3
Log P RDKit 2.91
Topological polar surface area (Å2) RDKit 87.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
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 15
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
Squarrosin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.78
Squarrosin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.17
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No