IMPPAT Phytochemical information: 
Isosalipurposide
Isosalipurposide
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)cc(c2C(=O)/C=C/c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H22O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-8,16,18-24,26-29H,9H2/b6-3+/t16-,18-,19+,20-,21-/m1/s1
InChIKey: WQCWELFQKXIPCN-JSYAWONVSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6C=O)/C=C/cccccc6))O)))))))))O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)c1ccccc1OC1CCCCO1
Scaffold Graph/Node level: OC(CCC1CCCCC1)C1CCCCC1OC1CCCCO1
Scaffold Graph level: CC(CCC1CCCCC1)C1CCCCC1CC1CCCCC1
Functional groups: CO; cO[C@@H](C)OC; cO; c/C=C/C(c)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Chalcones
Synonymous chemical names:
isosalipurposide (4,2',4',6'-tetrahydroxychalcone-2'-glucoside), phlorizin chalcone, isosalipurposide
External chemical identifiers:
CID:CID_5318659; ChEMBL:CHEMBL2430461; ChEBI:CHEBI:80486; ZINC:ZINC000013558213
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isosalipurposide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 434.4
Log P RDKit -0.12
Topological polar surface area (Å2) RDKit 177.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 6
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Isosalipurposide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.24
Isosalipurposide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No