IMPPAT Phytochemical information: 
Cimicifugic acid A
Cimicifugic acid A
Summary

SMILES: COc1cc(/C=C/C(=O)O[C@@H]([C@@](C(=O)O)(Cc2ccc(c(c2)O)O)O)C(=O)O)ccc1O
InChI: InChI=1S/C21H20O11/c1-31-16-9-11(2-6-14(16)23)4-7-17(25)32-18(19(26)27)21(30,20(28)29)10-12-3-5-13(22)15(24)8-12/h2-9,18,22-24,30H,10H2,1H3,(H,26,27)(H,28,29)/b7-4+/t18-,21-/m1/s1
InChIKey: LIJMMUDJSMCVDJ-ZHBFVYIWSA-N
DeepSMILES: COccc/C=C/C=O)O[C@@H][C@@]C=O)O))Ccccccc6)O))O))))))O))C=O)O)))))))ccc6O
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 a
External chemical identifiers:
CID:CID_6449879; ChEMBL:CHEMBL517537; ZINC:ZINC000015219306; FDASRS:0S0MJU107Z
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cimicifugic acid A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.38
Log P RDKit 0.88
Topological polar surface area (Å2) RDKit 191.05
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 32
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 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.19
Number of rotatable bonds RDKit 10
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 A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.18
Cimicifugic acid A
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 -8.00
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