IMPPAT Phytochemical information: 
(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(6R,7S,9S,10S,13S,15R,16R)-10,15-dihydroxy-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(6R,7S,9S,10S,13S,15R,16R)-10,15-dihydroxy-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2CC3CCC4C([C@]3(C[C@H]2O)C)C[C@@H]([C@]2(C4CC3C2[C@@H]([C@]2(O3)CCCCO2)C)C)O)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
InChI: InChI=1S/C38H62O15/c1-16-27-23(53-38(16)8-4-5-9-48-38)11-20-18-7-6-17-10-22(21(41)13-36(17,2)19(18)12-26(42)37(20,27)3)49-34-32(47)30(45)33(25(15-40)51-34)52-35-31(46)29(44)28(43)24(14-39)50-35/h16-35,39-47H,4-15H2,1-3H3/t16-,17?,18?,19?,20?,21+,22+,23?,24+,25+,26-,27?,28+,29-,30+,31+,32+,33-,34+,35-,36-,37+,38+/m0/s1
InChIKey: MTZLHTRAIKFJLJ-PYUCPRTRSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]CCCCCC[C@]6C[C@H]%10O)))C))C[C@@H][C@]C6CCC5[C@@H][C@]O5)CCCCO6))))))C))))))C))O)))))))))))[C@@H][C@H][C@H]6O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))O))O
Scaffold Graph/Node/Bond level: C1CCC(OC2CCC(OC3CCC4C(CCC5C4CCC4C6CC7(CCCCO7)OC6CC45)C3)OC2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCC(OC3CCC4C(CCC5C4CCC4C6CC7(CCCCO7)OC6CC45)C3)OC2)OC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCC4C(CCC5C4CCC4C6CC7(CCCCC7)CC6CC45)C3)CC2)CC1
Functional groups: CO; CO[C@](C)(C)OC; CO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Spirostane steroids
Synonymous chemical names:
bioside
External chemical identifiers:
CID:CID_3084119
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(6R,7S,9S,10S,13S,15R,16R)-10,15-dihydroxy-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 758.9
Log P RDKit -0.86
Topological polar surface area (Å2) RDKit 237.45
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 53
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 23
Stereochemical complexity RDKit 0.61
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 38
Shape complexity RDKit 1
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(6R,7S,9S,10S,13S,15R,16R)-10,15-dihydroxy-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.149955
(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(6R,7S,9S,10S,13S,15R,16R)-10,15-dihydroxy-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
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 -10.93
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