IMPPAT Phytochemical information: 
Sitoindoside IX
Sitoindoside IX
Summary

SMILES: OC[C@H]1O[C@@H](OCC2=C(C)C[C@@H](OC2=O)[C@H]([C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3C[C@@H]3[C@]4([C@]2(C)C(=O)C=C[C@@H]4O)O3)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C34H48O11/c1-15-11-22(43-30(41)18(15)14-42-31-29(40)28(39)27(38)23(13-35)44-31)16(2)19-5-6-20-17-12-26-34(45-26)25(37)8-7-24(36)33(34,4)21(17)9-10-32(19,20)3/h7-8,16-17,19-23,25-29,31,35,37-40H,5-6,9-14H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,25-,26+,27+,28-,29+,31+,32+,33-,34+/m0/s1
InChIKey: WKCJIGSUKSPCKI-WNXUODGFSA-N
DeepSMILES: OC[C@H]O[C@@H]OCC=CC)C[C@@H]OC6=O)))[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6C[C@@H][C@][C@]6C)C=O)C=C[C@@H]6O))))))O3)))))))))))))C))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OC(CC2CCC3C2CCC2C3CC3OC34CC=CC(=O)C24)CC=C1COC1CCCCO1
Scaffold Graph/Node level: OC1CCCC23OC2CC2C4CCC(CC5CCC(COC6CCCCO6)C(O)O5)C4CCC2C13
Scaffold Graph level: CC1CC(CC2CCC3C2CCC2C3CC3CC34CCCC(C)C24)CCC1CCC1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; CC1=C(C)C(=O)OCC1; C[C@H]1O[C@]1(C)C; CC=CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
sitoindoside ix, Sitoindoside IX, sitoindoside 9
External chemical identifiers:
CID:CID_189586; ChEMBL:CHEMBL1934467; ChEBI:CHEBI:69119; ZINC:ZINC000082190806
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sitoindoside IX
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 632.75
Log P RDKit 1.18
Topological polar surface area (Å2) RDKit 175.51
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.47
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 28
Shape complexity RDKit 0.82
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Sitoindoside IX
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
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 0.210039
Sitoindoside IX
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.97
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 Yes