IMPPAT Phytochemical information: 
Broussoaurone A

Broussoaurone A
Summary

SMILES: CC(=CCc1cc2c(cc1O)O/C(=C\c1ccc(c(c1)O)O)/C2=O)C
InChI: InChI=1S/C20H18O5/c1-11(2)3-5-13-9-14-18(10-16(13)22)25-19(20(14)24)8-12-4-6-15(21)17(23)7-12/h3-4,6-10,21-23H,5H2,1-2H3/b19-8-
InChIKey: NYCBUBKYUALZIH-UWVJOHFNSA-N
DeepSMILES: CC=CCcccccc6O)))O/C=C\cccccc6)O))O))))))/C5=O))))))))))C
Scaffold Graph/Node/Bond level: O=C1C(=Cc2ccccc2)Oc2ccccc21
Scaffold Graph/Node level: OC1C(CC2CCCCC2)OC2CCCCC21
Scaffold Graph level: CC1C(CC2CCCCC2)CC2CCCCC21
Functional groups: CC=C(C)C; cO; c/C=C1\OccC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Aurone flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Aurones
Synonymous chemical names:
broussoaurone a
External chemical identifiers:
CID:CID_15298907; ChEMBL:CHEMBL463019; ZINC:ZINC000014819131
Chemical structure download


Broussoaurone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 338.36
Log P RDKit 3.93
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
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 17
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Broussoaurone A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.45


Broussoaurone A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.20
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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