IMPPAT Phytochemical information: 
4-Hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside
4-Hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside
Summary

SMILES: CCCCCCCCCCCCCCCC(=O)OCC1OC(OCC2=C(C)CC(OC2=O)C(C2CCC3C2(C)CCC2C3CC3C4(C2(C)C(=O)C=CC4O)O3)C)C(C(C1O)O)O
InChI: InChI=1S/C50H78O12/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-42(53)58-29-38-43(54)44(55)45(56)47(61-38)59-28-33-30(2)26-37(60-46(33)57)31(3)34-20-21-35-32-27-41-50(62-41)40(52)23-22-39(51)49(50,5)36(32)24-25-48(34,35)4/h22-23,31-32,34-38,40-41,43-45,47,52,54-56H,6-21,24-29H2,1-5H3
InChIKey: AGNOSYRBHQJIEE-UHFFFAOYSA-N
DeepSMILES: CCCCCCCCCCCCCCCC=O)OCCOCOCC=CC)CCOC6=O)))CCCCCC5C)CCCC6CCCC6C)C=O)C=CC6O))))))O3)))))))))))))C))))))))CCC6O))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: COC(C)=O; COC(OC)C; CC1=C(C)C(=O)OCC1; CC1OC1(C)C; CC=CC(=O)C; CO
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 x, Sitoindoside X
External chemical identifiers:
CID:CID_189702
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
4-Hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 871.16
Log P RDKit 7.21
Topological polar surface area (Å2) RDKit 181.58
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 50
Number of heavy atoms RDKit 62
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 43
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 22
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
4-Hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 0.05
4-Hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 6-o-hexadecanoylhexopyranoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.20
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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