IMPPAT Phytochemical information: 
Cimicifugic acid G
Cimicifugic acid G
Summary

SMILES: COc1cc(/C=C/C(=O)O[C@@H]([C@@](C(=O)O)(Cc2ccc(c(c2)O)O)O)C(=O)O)ccc1OC
InChI: InChI=1S/C22H22O11/c1-31-16-7-4-12(10-17(16)32-2)5-8-18(25)33-19(20(26)27)22(30,21(28)29)11-13-3-6-14(23)15(24)9-13/h3-10,19,23-24,30H,11H2,1-2H3,(H,26,27)(H,28,29)/b8-5+/t19-,22-/m1/s1
InChIKey: YMPYAGUNPNITIL-AHKCGJDQSA-N
DeepSMILES: COccc/C=C/C=O)O[C@@H][C@@]C=O)O))Ccccccc6)O))O))))))O))C=O)O)))))))ccc6OC
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCCCC1CCCCC1
Scaffold Graph level: CC(CCCCC1CCCCC1)CCC1CCCCC1
Functional groups: cOC; c/C=C/C(=O)OC; CC(=O)O; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
cimicifugic acid g
External chemical identifiers:
CID:CID_11655574; ChEMBL:CHEMBL479308; ZINC:ZINC000015219333
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cimicifugic acid G
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 462.41
Log P RDKit 1.18
Topological polar surface area (Å2) RDKit 180.05
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.23
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Cimicifugic acid G
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
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 0.19
Cimicifugic acid G
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.85
Number of PAINS structural alerts SwissADME 1
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