IMPPAT Phytochemical information: 
Fukinolic acid
Fukinolic acid
Summary

SMILES: O=C(O[C@@H]([C@@](C(=O)O)(Cc1ccc(c(c1)O)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C20H18O11/c21-12-4-1-10(7-14(12)23)3-6-16(25)31-17(18(26)27)20(30,19(28)29)9-11-2-5-13(22)15(24)8-11/h1-8,17,21-24,30H,9H2,(H,26,27)(H,28,29)/b6-3+/t17-,20-/m1/s1
InChIKey: ACYXDIZTQDLTCB-UVIKLTKHSA-N
DeepSMILES: O=CO[C@@H][C@@]C=O)O))Ccccccc6)O))O))))))O))C=O)O))))/C=C/cccccc6)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: 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:
fukinolic acid
External chemical identifiers:
CID:CID_6441059; ChEMBL:CHEMBL487192; ZINC:ZINC000031155506; FDASRS:OLL8DU5J30; SureChEMBL:SCHEMBL18371556
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Fukinolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 434.35
Log P RDKit 0.58
Topological polar surface area (Å2) RDKit 202.05
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 31
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 3
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 9
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
Fukinolic acid
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 0.17
Fukinolic acid
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 -8.15
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 No