IMPPAT Phytochemical information: 
Cimicifugin

Cimicifugin
Summary

SMILES: CC1CC2(CO[C@]3(C1C1(C)CCC45C(C1(C3O)C)CCC1C5(C4)CCC(C1(C)C)O)O2)C(C)C
InChI: InChI=1S/C30H48O4/c1-17(2)29-14-18(3)22-25(6)12-13-28-15-27(28)11-10-21(31)24(4,5)19(27)8-9-20(28)26(25,7)23(32)30(22,34-29)33-16-29/h17-23,31-32H,8-16H2,1-7H3/t18?,19?,20?,21?,22?,23?,25?,26?,27?,28?,29?,30-/m1/s1
InChIKey: SUGCQRXFUUJLDY-OPJGURERSA-N
DeepSMILES: CCCCCO[C@]C7CC)CCCCC6C9O))C))CCCC6C7)CCCC6C)C))O))))))))))))))O5))))CC)C
Scaffold Graph/Node/Bond level: C1CCC23CC24CCC2C(CC56OCC(CCC25)O6)C4CCC3C1
Scaffold Graph/Node level: C1CCC23CC24CCC2C(CC56OCC(CCC25)O6)C4CCC3C1
Scaffold Graph level: C1CCC23CC24CCC2C(CC56CCC(CCC25)C6)C4CCC3C1
Functional groups: C[C@]1(C)OCCO1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cycloartane triterpenoids
Synonymous chemical names:
cimicifugin
External chemical identifiers:
CID:CID_45048779
Chemical structure download


Cimicifugin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 472.71
Log P RDKit 5.54
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 30
Shape complexity RDKit 1
Number of rotatable bonds RDKit 1
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 5
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7


Cimicifugin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.525664


Cimicifugin
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 High
Log Kp (Skin permeation, cm/s) SwissADME -4.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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