IMPPAT Phytochemical information: 
[(1S,1'R,3'R,4R,4'R,5S,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-1,4',6',12',17',17'-hexamethylspiro[6-oxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
[(1S,1'R,3'R,4R,4'R,5S,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-1,4',6',12',17',17'-hexamethylspiro[6-oxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1C[C@]23C[C@]43CC[C@@H](C([C@@H]4CC[C@H]2[C@]2([C@@]1(C)[C@@H]1[C@H](C2)O[C@@]2(C[C@H]1C)CC[C@]1([C@@H]2O1)C)C)(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)OC(=O)C)O
InChI: InChI=1S/C40H60O10/c1-20-15-40(14-13-36(7)33(40)50-36)49-24-16-35(6)26-10-9-25-34(4,5)27(48-32-30(44)31(47-22(3)42)23(43)18-45-32)11-12-38(25)19-39(26,38)17-28(46-21(2)41)37(35,8)29(20)24/h20,23-33,43-44H,9-19H2,1-8H3/t20-,23-,24+,25+,26+,27+,28-,29+,30-,31+,32+,33+,35+,36+,37-,38-,39+,40-/m1/s1
InChIKey: ZFGRVWJBDIFZRK-QNDJKQGNSA-N
DeepSMILES: CC=O)O[C@@H]C[C@@]C[C@@]3CC[C@@H]C[C@@H]6CC[C@H]%11[C@][C@@]%15C)[C@@H][C@H]C5)O[C@@]C[C@H]6C)))CC[C@][C@@H]5O3))C)))))))))C))))))C)C))O[C@@H]OC[C@H][C@@H][C@H]6O))OC=O)C))))O
Scaffold Graph/Node/Bond level: C1CCC(OC2CCC34CC35CCC3C6CCC7(CCC8OC87)OC6CC3C5CCC4C2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCC34CC35CCC3C6CCC7(CCC8OC87)OC6CC3C5CCC4C2)OC1
Scaffold Graph level: C1CCC(CC2CCC34CC35CCC3C6CCC7(CCC8CC87)CC6CC3C5CCC4C2)CC1
Functional groups: C[C@@]1(C)O[C@@H]1C; CC(=O)OC; CO[C@@H](OC)C; CO; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Cycloartanols and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cycloartane triterpenoids
Synonymous chemical names:
3-o-acetylactein, 3-o-acetyl-23-epi-26-deoxyactein
External chemical identifiers:
CID:CID_46881251; ChEMBL:CHEMBL1077046; ZINC:ZINC000095549005
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,1'R,3'R,4R,4'R,5S,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-1,4',6',12',17',17'-hexamethylspiro[6-oxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 700.91
Log P RDKit 5.09
Topological polar surface area (Å2) RDKit 133.28
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 50
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 18
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 38
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 6
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 6
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 9
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
[(1S,1'R,3'R,4R,4'R,5S,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-1,4',6',12',17',17'-hexamethylspiro[6-oxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
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 0.23
[(1S,1'R,3'R,4R,4'R,5S,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-1,4',6',12',17',17'-hexamethylspiro[6-oxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.89
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No