IMPPAT Phytochemical information: 
(+)-Usnic acid

(+)-Usnic acid
Summary

SMILES: CC(=O)C1=C(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/h5,21-23H,1-4H3
InChIKey: WEYVVCKOOFYHRW-UHFFFAOYSA-N
DeepSMILES: CC=O)C=CO)C=CCC6=O))C)ccO)cC)ccc6O9))C=O)C)))O
Scaffold Graph/Node/Bond level: O=C1C=CC=C2Oc3ccccc3C12
Scaffold Graph/Node level: OC1CCCC2OC3CCCCC3C12
Scaffold Graph level: CC1CCCC2CC3CCCCC3C12
Functional groups: cC(C)=O; cO; cOC1=CC(O)=C(C(C)=O)C(=O)C1
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, d-
External chemical identifiers:
CID:24211; ChEMBL:CHEMBL242022; ChEBI:38319; FDASRS:0W584PFJ77; SureChEMBL:SCHEMBL1767536
Chemical structure download


(+)-Usnic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.32
Log P RDKit 2.13
Topological polar surface area (Å2) RDKit 121.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
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 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.28
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 0.5548


(+)-Usnic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.86
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No