IMPPAT Phytochemical information: 
Usnic acid

Usnic acid
Summary

SMILES: CC(=O)C1C(=O)C=C2C(C1=O)(C)c1c(O)c(C)c(c(c1O2)C(=O)C)O
InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
InChIKey: CUCUKLJLRRAKFN-UHFFFAOYSA-N
DeepSMILES: CC=O)CC=O)C=CCC6=O))C)ccO)cC)ccc6O9))C=O)C)))O
Scaffold Graph/Node/Bond level: O=C1C=C2Oc3ccccc3C2C(=O)C1
Scaffold Graph/Node level: OC1CC(O)C2C(C1)OC1CCCCC12
Scaffold Graph level: CC1CC(C)C2C(C1)CC1CCCCC12
Functional groups: CC(C)=O; cC(C)=O; cO; cOC(C)=CC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Acetophenones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Aromatic polyketides
NP Classifier Class: Usnic acid and derivatives
Synonymous chemical names:
usnic acid, usnic acidd-
External chemical identifiers:
CID:5646; ChEMBL:CHEMBL1375951; ChEBI:2264; SureChEMBL:SCHEMBL177774; MolPort-001-832-622
Chemical structure download


Usnic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


Usnic acid
Drug-likeness
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 Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6163


Usnic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.36
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
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


Usnic acid
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1700
ENSP00000216037XBP1700
ENSP00000225577RPS6KB1700
ENSP00000263025MAPK3700
ENSP00000282077PDK1700
ENSP00000311032CASP3700
ENSP00000340691EIF4EBP1700
ENSP00000358327CASP7700
ENSP00000374455SQSTM1700
ENSP00000388566CASP4700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.