IMPPAT Phytochemical information: 
Hibiscone A

Hibiscone A
Summary

SMILES: CC([C@H]1CCc2c3[C@@H]1C[C@H](C)C(=O)c3oc2)C
InChI: InChI=1S/C15H20O2/c1-8(2)11-5-4-10-7-17-15-13(10)12(11)6-9(3)14(15)16/h7-9,11-12H,4-6H2,1-3H3/t9-,11+,12+/m0/s1
InChIKey: OXGBVJBYGGQURY-MVWJERBFSA-N
DeepSMILES: CC[C@H]CCcc[C@@H]6C[C@H]C)C=O)c6oc9))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CCC2CCCc3coc1c32
Scaffold Graph/Node level: OC1CCC2CCCC3COC1C23
Scaffold Graph level: CC1CCC2CCCC3CCC1C23
Functional groups: cC(=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzofurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Cadinane sesquiterpenoids
Synonymous chemical names:
hibiscone a
External chemical identifiers:
CID:CID_102239770; ZINC:ZINC000085866982
Chemical structure download


Hibiscone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 232.32
Log P RDKit 3.8
Topological polar surface area (Å2) RDKit 30.21
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
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


Hibiscone A
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 0.736775


Hibiscone A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No