IMPPAT Phytochemical information: 
Nandinin
Nandinin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)C(C#N)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C23H23NO10/c24-10-17(28)13-3-5-14(6-4-13)32-23-21(31)20(30)22(18(11-25)33-23)34-19(29)8-2-12-1-7-15(26)16(27)9-12/h1-9,17-18,20-23,25-28,30-31H,11H2/b8-2+/t17?,18-,20-,21-,22-,23-/m1/s1
InChIKey: OTBWOFBYEYFNNC-YDWCALSJSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6))CC#N))O)))))))[C@@H][C@H][C@@H]6OC=O)/C=C/cccccc6)O))O))))))))))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC(Oc2ccccc2)OC1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC(OC2CCCCC2)OC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC(CC2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; CC#N; c/C=C/C(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
nandinin
External chemical identifiers:
CID:CID_6442984
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Nandinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 473.43
Log P RDKit 0.1
Topological polar surface area (Å2) RDKit 189.93
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 1
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 8
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
Nandinin
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 0
Ghose rule RDKit Passed
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 0.14
Nandinin
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 -9.00
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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