IMPPAT Phytochemical information: 
Retusin 7-O-neohesperidoside
Retusin 7-O-neohesperidoside
Summary

SMILES: OCC1O[C@@H](Oc2ccc3c(c2O)occ(c3=O)c2ccc(cc2)OC)C([C@H]([C@@H]1O)O)O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O
InChI: InChI=1S/C28H32O14/c1-11-18(30)22(34)24(36)27(39-11)42-26-23(35)20(32)17(9-29)41-28(26)40-16-8-7-14-19(31)15(10-38-25(14)21(16)33)12-3-5-13(37-2)6-4-12/h3-8,10-11,17-18,20,22-24,26-30,32-36H,9H2,1-2H3/t11?,17?,18-,20+,22-,23-,24?,26?,27-,28+/m0/s1
InChIKey: BLCSJLFCYHDNBE-ZQHCIKKUSA-N
DeepSMILES: OCCO[C@@H]Occcccc6O))occc6=O))cccccc6))OC)))))))))))))))C[C@H][C@@H]6O))O))O[C@@H]OCC)[C@@H][C@@H]C6O))O))O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2cc(OC3OCCCC3OC3CCCCO3)ccc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CC(OC3OCCCC3OC3CCCCO3)CCC21
Scaffold Graph level: CC1C(C2CCCCC2)CCC2CC(CC3CCCCC3CC3CCCCC3)CCC21
Functional groups: CO; CO[C@@H](C)OC; cO[C@@H](C)OC; cO; coc; c=O; cOC
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:
retusin-7-o-neohesperidoside
External chemical identifiers:
CID:CID_44257256
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Retusin 7-O-neohesperidoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 592.55
Log P RDKit -0.8
Topological polar surface area (Å2) RDKit 217.97
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.46
Number of rotatable bonds RDKit 7
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Retusin 7-O-neohesperidoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
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 0.18
Retusin 7-O-neohesperidoside
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 -10.24
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