IMPPAT Phytochemical information: 
Sitoindoside I
Sitoindoside I
Summary

SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4CC[C@@H]3[C@@H](CC[C@H](C(C)C)CC)C)C)C2)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C51H90O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-45(52)56-34-44-46(53)47(54)48(55)49(58-44)57-39-29-31-50(6)38(33-39)25-26-40-42-28-27-41(51(42,7)32-30-43(40)50)36(5)23-24-37(9-2)35(3)4/h25,35-37,39-44,46-49,53-55H,8-24,26-34H2,1-7H3/t36-,37-,39+,40+,41-,42+,43+,44-,46-,47+,48-,49-,50+,51-/m1/s1
InChIKey: JCLYMCVRBRHEHI-TWDDPRSNSA-N
DeepSMILES: CCCCCCCCCCCCCCCC=O)OC[C@H]O[C@@H]O[C@H]CC[C@]C=CC[C@@H][C@@H]6CC[C@][C@H]6CC[C@@H]5[C@@H]CC[C@H]CC)C))CC)))))C))))))C))))))))C6))C))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=C2CC(OC3CCCCO3)CCC2C2CCC3CCCC3C2C1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(CCC4C5CCCC5CCC34)C2)OC1
Scaffold Graph level: C1CCC(CC2CCC3C(CCC4C5CCCC5CCC34)C2)CC1
Functional groups: COC(C)=O; CO[C@@H](C)OC; CO; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Stigmastanes and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Stigmastane steroids
Synonymous chemical names:
Sitoindoside I, sitoindoside i, sitoindosides i, stioindoside i, sterylac-ylglucosides-sitoindoside i
External chemical identifiers:
CID:CID_9832350; ChEMBL:CHEMBL4452244; ChEBI:CHEBI:67595; ZINC:ZINC000095876436; MolPort-035-706-296
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sitoindoside I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 815.27
Log P RDKit 11.88
Topological polar surface area (Å2) RDKit 105.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 51
Number of heavy atoms RDKit 58
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 48
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 25
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Sitoindoside I
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 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.05061
Sitoindoside I
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Insoluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -0.56
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 Yes
P-glycoprotein substrate SwissADME Yes