IMPPAT Phytochemical information: 
Rothindin
Rothindin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc3c(c2)OCO3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H20O10/c23-7-17-19(25)20(26)21(27)22(32-17)31-11-2-3-12-15(6-11)28-8-13(18(12)24)10-1-4-14-16(5-10)30-9-29-14/h1-6,8,17,19-23,25-27H,7,9H2/t17-,19-,20+,21-,22-/m1/s1
InChIKey: GWACEFYEIOPAJV-MIUGBVLSSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6)occc6=O))cccccc6)OCO5)))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccc3c(c2)OCO3)coc2cc(OC3CCCCO3)ccc12
Scaffold Graph/Node level: OC1C(C2CCC3OCOC3C2)COC2CC(OC3CCCCO3)CCC21
Scaffold Graph level: CC1C2CCC(CC3CCCCC3)CC2CCC1C1CCC2CCCC2C1
Functional groups: CO; cO[C@@H](C)OC; coc; c=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavonoid O-glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
rothindin, Rothindin
External chemical identifiers:
CID:CID_3085261; ChEBI:CHEBI:169282; ZINC:ZINC000059728167
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rothindin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 444.39
Log P RDKit 0.37
Topological polar surface area (Å2) RDKit 148.05
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 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5
Rothindin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.444692
Rothindin
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 -8.42
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 No