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
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Usnic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.32
Log P RDKit 1.5
Topological polar surface area (Å2) RDKit 117.97
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
Usnic 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 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
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.