IMPPAT Phytochemical information: 
Trifolirhizin
Trifolirhizin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)OC[C@@H]2[C@H]3Oc3c2cc2c(c3)OCO2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1
InChIKey: VGSYCWGXBYZLLE-QEEQPWONSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6)OC[C@@H][C@H]6Occ5cccc6)OCO5)))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1cc2c(cc1OC1CCCCO1)OCC1c3cc4c(cc3OC21)OCO4
Scaffold Graph/Node level: C1CCC(OC2CCC3C(C2)OCC2C4CC5OCOC5CC4OC32)OC1
Scaffold Graph level: C1CCC(CC2CCC3C(CCC4C5CC6CCCC6CC5CC34)C2)CC1
Functional groups: CO; cO[C@@H](C)OC; cOC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Furanoisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Pterocarpan
Synonymous chemical names:
trifolirhizin, (-)-maackiain-3-o-glucoside, Trifolirhizin
External chemical identifiers:
CID:CID_442827; ChEMBL:CHEMBL454878; ChEBI:CHEBI:9714; ZINC:ZINC000004098749; MolPort-001-742-236
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Trifolirhizin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 446.41
Log P RDKit 0.2
Topological polar surface area (Å2) RDKit 136.3
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6
Trifolirhizin
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 Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.52
Trifolirhizin
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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.45
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 No
P-glycoprotein substrate SwissADME Yes