IMPPAT Phytochemical information: 
Filicinic acid

Filicinic acid
Summary

SMILES: OC1=CC(=O)C(C(=C1)O)(C)C
InChI: InChI=1S/C8H10O3/c1-8(2)6(10)3-5(9)4-7(8)11/h3-4,9-10H,1-2H3
InChIKey: ZAQQZMZXYOTJAB-UHFFFAOYSA-N
DeepSMILES: OC=CC=O)CC=C6)O))C)C
Scaffold Graph/Node/Bond level: O=C1C=CC=CC1
Scaffold Graph/Node level: OC1CCCCC1
Scaffold Graph level: CC1CCCCC1
Functional groups: O=C1C=C(O)C=C(O)C1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Vinylogous acids
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Cyclic polyketides
NP Classifier Class: Simple cyclic polyketides
Synonymous chemical names:
filicinic acid, Filicinic acid
External chemical identifiers:
CID:CID_550690
Chemical structure download


Filicinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 154.17
Log P RDKit 1.48
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 11
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1


Filicinic acid
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.555207


Filicinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.75
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