IMPPAT Phytochemical information: 
Fraxinellone

Fraxinellone
Summary

SMILES: CC1=C2C(=O)O[C@H]([C@@]2(CCC1)C)c1cocc1
InChI: InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14+/m0/s1
InChIKey: XYYAFLHHHZVPRN-GXTWGEPZSA-N
DeepSMILES: CC=CC=O)O[C@H][C@@]5CCC9)))C))ccocc5
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)C2CCCC=C12
Scaffold Graph/Node level: OC1OC(C2CCOC2)C2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC2)C2CCCCC12
Functional groups: CC(=C1CCOC1=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isobenzofurans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
Synonymous chemical names:
Fraxinellone, fraxinellone
External chemical identifiers:
CID:CID_124039; ChEMBL:CHEMBL257170; ZINC:ZINC000000265490; SureChEMBL:SCHEMBL17503653; MolPort-006-828-762
Chemical structure download


Fraxinellone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 232.28
Log P RDKit 3.38
Topological polar surface area (Å2) RDKit 39.44
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Fraxinellone
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 0.7


Fraxinellone
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 -5.96
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No