IMPPAT Phytochemical information: 
Licoisoflavone A 7-O-glucoside
Licoisoflavone A 7-O-glucoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2O)CC=C(C)C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C26H28O11/c1-11(2)3-4-13-15(28)6-5-14(22(13)31)18-9-17(30)21-16(29)7-12(8-19(21)36-18)35-26-25(34)24(33)23(32)20(10-27)37-26/h3,5-9,20,23-29,31-34H,4,10H2,1-2H3/t20-,23-,24+,25-,26-/m1/s1
InChIKey: RBHVNJRQJYAUPH-DDLBMNSQSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6)occc6=O)))cccccc6O))CC=CC)C)))))O)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2cc(OC3CCCCO3)ccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC(OC3CCCCO3)CCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC(CC3CCCCC3)CCC12
Functional groups: CO; cO[C@@H](C)OC; cO; coc; c=O; CC=C(C)C
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: Flavones
Synonymous chemical names:
7-o-beta-d-glucopyranoside-licoisoflavone a
External chemical identifiers:
CID:CID_101049552
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Licoisoflavone A 7-O-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 516.5
Log P RDKit 1.26
Topological polar surface area (Å2) RDKit 190.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.35
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
Licoisoflavone A 7-O-glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.233523
Licoisoflavone A 7-O-glucoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.73
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 Yes