IMPPAT Phytochemical information: 
[(1'S,3'R,4'R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-13-ene]-3'-yl] acetate
[(1'S,3'R,4'R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-13-ene]-3'-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1C[C@]23C[C@]43CC[C@@H](C([C@@H]4CC=C2[C@]2([C@@]1(C)[C@H]1[C@H](C)CC3(O[C@H]1C2)OC(C1(C3O1)C)O)C)(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C37H54O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h9,17,19-21,23-30,39-42H,8,10-16H2,1-7H3/t17-,19-,20+,21+,23+,24-,25+,26+,27-,28+,29?,30?,32+,33-,34?,35-,36+,37?/m1/s1
InChIKey: XUJMHSCMPCZWOV-UJAIUVFWSA-N
DeepSMILES: CC=O)O[C@@H]C[C@@]C[C@@]3CC[C@@H]C[C@@H]6CC=C%11[C@][C@@]%15C)[C@H][C@H]C)CCO[C@H]6C9)))OCCC5O3))C))O))))))))C))))))C)C))O[C@@H]OC[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=C2C3CC4OC5(CCC4C3CCC23CC32CCC(OC3CCCCO3)CC2C1)OCC1OC15
Scaffold Graph/Node level: C1CCC(OC2CCC34CC35CCC3C6CCC7(OCC8OC87)OC6CC3C5CCC4C2)OC1
Scaffold Graph level: C1CCC(CC2CCC34CC35CCC3C6CCC7(CCC8CC87)CC6CC3C5CCC4C2)CC1
Functional groups: CC(=O)OC; CC=C(C)C; CC1(OC)OC(O)C2(C)OC12; CO[C@@H](OC)C; CO
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:
cimicifugoside
External chemical identifiers:
CID:CID_441913; ChEBI:CHEBI:3700
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1'S,3'R,4'R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-13-ene]-3'-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 674.83
Log P RDKit 2.95
Topological polar surface area (Å2) RDKit 156.67
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 18
Stereochemical complexity RDKit 0.49
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 34
Shape complexity RDKit 0.92
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 4
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 4
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
[(1'S,3'R,4'R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-13-ene]-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 Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2
[(1'S,3'R,4'R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-13-ene]-3'-yl] acetate
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 -8.61
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 No
P-glycoprotein substrate SwissADME Yes