IMPPAT Phytochemical information: 
Cimicifugic acid F
Cimicifugic acid F
Summary

SMILES: COc1ccc(cc1O)/C=C/C(=O)O[C@@H]([C@@](C(=O)O)(Cc1ccc(cc1)O)O)C(=O)O
InChI: InChI=1S/C21H20O10/c1-30-16-8-4-12(10-15(16)23)5-9-17(24)31-18(19(25)26)21(29,20(27)28)11-13-2-6-14(22)7-3-13/h2-10,18,22-23,29H,11H2,1H3,(H,25,26)(H,27,28)/b9-5+/t18-,21-/m1/s1
InChIKey: WBGMKAAMRFEBHK-PZTMCFHLSA-N
DeepSMILES: COcccccc6O)))/C=C/C=O)O[C@@H][C@@]C=O)O))Ccccccc6))O))))))O))C=O)O
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; cO; c/C=C/C(=O)OC; CC(=O)O; 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 f
External chemical identifiers:
CID:CID_6450179; ChEMBL:CHEMBL1097936; ZINC:ZINC000033985277; FDASRS:5586G4WLE3
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cimicifugic acid F
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 432.38
Log P RDKit 1.17
Topological polar surface area (Å2) RDKit 170.82
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
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 F
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.286123
Cimicifugic acid F
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 -7.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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