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: cOC1=CC(O)=C(C(C)=O)C(=O)C1; cO; 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, d-, Usnic acid, d-
External chemical identifiers:
CID:CID_24211; ChEMBL:CHEMBL242022; ChEBI: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
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 0.55481


(+)-Usnic acid
ADME 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
Number of Brenk structural alerts SwissADME 1
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


(+)-Usnic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000428ENSG00000165140FBP12203NPASS