IMPPAT Phytochemical information: 
Licoagroside A
Licoagroside A
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(OC)c(cc2c2coc3c(c2=O)cc(c(c3)O)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C23H24O12/c1-31-16-4-10-14(5-13(16)26)33-8-11(19(10)27)9-3-12(25)17(32-2)6-15(9)34-23-22(30)21(29)20(28)18(7-24)35-23/h3-6,8,18,20-26,28-30H,7H2,1-2H3/t18-,20-,21+,22-,23-/m1/s1
InChIKey: RQLOWOYMKFVTBB-DODNOZFWSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccOC))ccc6ccoccc6=O))cccc6)O))OC)))))))))))O))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2OC2CCCCO2)coc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OCC1C1CCCCC1OC1CCCCO1
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCCCC1CC1CCCCC1
Functional groups: CO; cO[C@@H](C)OC; cOC; coc; c=O; cO
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:
licoagroside a(isoflavone glycoside), licoagroside a
External chemical identifiers:
CID:CID_73357140; ChEMBL:CHEMBL2437366; ZINC:ZINC000096937720
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Licoagroside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 492.43
Log P RDKit 0.07
Topological polar surface area (Å2) RDKit 188.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
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
Licoagroside A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
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 0.27
Licoagroside A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -9.13
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes