IMPPAT Phytochemical information: 
Boennin

Boennin
Summary

SMILES: COc1ccc2c(c1Oc1c(O)cc(c3c1oc(=O)cc3)O)oc(=O)cc2
InChI: InChI=1S/C19H12O8/c1-24-13-5-2-9-3-6-14(22)25-16(9)19(13)27-18-12(21)8-11(20)10-4-7-15(23)26-17(10)18/h2-8,20-21H,1H3
InChIKey: UOWOBKCJCCNEOP-UHFFFAOYSA-N
DeepSMILES: COcccccc6OccO)cccc6oc=O)cc6))))))O)))))))oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2cccc(Oc3cccc4ccc(=O)oc34)c2o1
Scaffold Graph/Node level: OC1CCC2CCCC(OC3CCCC4CCC(O)OC43)C2O1
Scaffold Graph level: CC1CCC2CCCC(CC3CCCC4CCC(C)CC43)C2C1
Functional groups: cOC; cOc; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Hydroxycoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
boennin
External chemical identifiers:
CID:CID_15380215; ZINC:ZINC000013378572
Chemical structure download


Boennin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.3
Log P RDKit 3.11
Topological polar surface area (Å2) RDKit 119.34
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 8
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 18
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.05
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
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 4


Boennin
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.529477


Boennin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.64
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 No
P-glycoprotein substrate SwissADME No