IMPPAT Phytochemical information: 
Cimifugoside
Cimifugoside
Summary

SMILES: CC(=O)O[C@@H]1[C@H](O)[C@]23C[C@]43CC[C@@H](C([C@@H]4CC=C2[C@]2([C@@]1(C)[C@@H]([C@@H](CC(=O)[C@@H]1OC1(C)C)C)C(=O)C2)C)(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C37H54O11/c1-17(13-19(39)29-33(5,6)48-29)25-20(40)14-34(7)23-10-9-22-32(3,4)24(47-31-27(43)26(42)21(41)15-45-31)11-12-36(22)16-37(23,36)28(44)30(35(25,34)8)46-18(2)38/h10,17,21-22,24-31,41-44H,9,11-16H2,1-8H3/t17-,21-,22+,24+,25+,26+,27-,28+,29+,30-,31+,34+,35+,36-,37+/m1/s1
InChIKey: QBLIDWUUYJDEPL-MZNPMZDBSA-N
DeepSMILES: CC=O)O[C@@H][C@H]O)[C@@]C[C@@]3CC[C@@H]C[C@@H]6CC=C%11[C@][C@@]%15C)[C@@H][C@@H]CC=O)[C@@H]OC3C)C))))))C))C=O)C5))))C))))))C)C))O[C@@H]OC[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(CCC1C(=O)CC2C3=CCC4CC(OC5CCCCO5)CCC45CC35CCC12)C1CO1
Scaffold Graph/Node level: OC(CCC1C(O)CC2C1CCC13CC14CCC(OC1CCCCO1)CC4CCC23)C1CO1
Scaffold Graph level: CC(CCC1C(C)CC2C1CCC13CC14CCC(CC1CCCCC1)CC4CCC23)C1CC1
Functional groups: CC(=O)OC; CO; CC=C(C)C; CC(=O)[C@@H]1OC1(C)C; CC(=O)C; CO[C@@H](OC)C
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:
cimifugoside
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cimifugoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 674.83
Log P RDKit 2.63
Topological polar surface area (Å2) RDKit 172.35
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 15
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 32
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
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 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Cimifugoside
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 0.18
Cimifugoside
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 -9.44
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