IMPPAT Phytochemical information: 
Sitoindoside IV
Sitoindoside IV
Summary

SMILES: CCCCCCCCCCCCCCCC(=O)OC1C(OCC2OC(OC3CCC4(C(=CCC5C4CCC4(C5CCC4C(CCC(C(C)C)CC)C)C)C3)C)C(C(C2O)O)O)C(O)C(C(C1O)O)O
InChI: InChI=1S/C57H100O12/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-45(58)69-54-51(64)49(62)48(61)50(63)53(54)66-34-44-46(59)47(60)52(65)55(68-44)67-39-29-31-56(6)38(33-39)25-26-40-42-28-27-41(57(42,7)32-30-43(40)56)36(5)23-24-37(9-2)35(3)4/h25,35-37,39-44,46-55,59-65H,8-24,26-34H2,1-7H3
InChIKey: IWPRSBXDWFAINE-UHFFFAOYSA-N
DeepSMILES: CCCCCCCCCCCCCCCC=O)OCCOCCOCOCCCCC=CCCC6CCCC6CCC5CCCCCC)C))CC)))))C))))))C))))))))C6))C))))))CCC6O))O))O)))))))CO)CCC6O))O))O
Scaffold Graph/Node/Bond level: C1=C2CC(OC3CCCC(COC4CCCCC4)O3)CCC2C2CCC3CCCC3C2C1
Scaffold Graph/Node level: C1CCC(OCC2CCCC(OC3CCC4C(CCC5C6CCCC6CCC45)C3)O2)CC1
Scaffold Graph level: C1CCC(CCC2CCCC(CC3CCC4C(CCC5C6CCCC6CCC45)C3)C2)CC1
Functional groups: CO; COC(C)=O; COC; CC=C(C)C; COC(OC)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 4, Sitoindoside IV, sitoindosides iv, sitoindoside iv
External chemical identifiers:
CID:CID_127197
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sitoindoside IV
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 977.42
Log P RDKit 9.09
Topological polar surface area (Å2) RDKit 195.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 57
Number of heavy atoms RDKit 69
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 20
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 54
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 27
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Sitoindoside IV
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 4
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.02
Sitoindoside IV
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Insoluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.47
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