IMPPAT Phytochemical information: 
Ncnuksmlrptjbc-nxtblzeosa-
Ncnuksmlrptjbc-nxtblzeosa-
Summary

SMILES: OC[C@H]1O[C@@H](OCC2=CC(=O)C3=C(C)C[C@@H]([C@@H]4[C@@H]([C@@H]23)OC(=O)C4=C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H26O10/c1-7-3-10(23)14-8(2)20(28)31-19(14)15-9(4-11(24)13(7)15)6-29-21-18(27)17(26)16(25)12(5-22)30-21/h4,10,12,14-19,21-23,25-27H,2-3,5-6H2,1H3/t10-,12+,14+,15-,16+,17-,18+,19-,21+/m0/s1
InChIKey: NCNUKSMLRPTJBC-NXTBLZEOSA-N
DeepSMILES: OC[C@H]O[C@@H]OCC=CC=O)C=CC)C[C@@H][C@@H][C@@H][C@@H]%107)OC=O)C5=C))))))O))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C1CCC=C1C(=O)C=C(COC3CCCCO3)C12
Scaffold Graph/Node level: CC1C(O)OC2C1CCCC1C(O)CC(COC3CCCCO3)C12
Scaffold Graph level: CC1CC2C(CCCC3C(C)CC(CCC4CCCCC4)C32)C1C
Functional groups: CO; CO[C@@H](C)OC; CC1=CC(=O)C(=C(C)C)C1; C=C1CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Guaiane sesquiterpenoids
Synonymous chemical names:
picriside a
External chemical identifiers:
CID:CID_21636022; ZINC:ZINC000146799585; SureChEMBL:SCHEMBL16029264
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ncnuksmlrptjbc-nxtblzeosa-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.43
Log P RDKit -1.89
Topological polar surface area (Å2) RDKit 162.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
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 4
Ncnuksmlrptjbc-nxtblzeosa-
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 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 0.25
Ncnuksmlrptjbc-nxtblzeosa-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.61
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No