IMPPAT Phytochemical information: 
Cycloartobiloxanthone
Cycloartobiloxanthone
Summary

SMILES: Oc1cc(O)c2c3c1-c1oc4c5C=CC(Oc5cc(c4c(=O)c1CC3C(O2)(C)C)O)(C)C
InChI: InChI=1S/C25H22O7/c1-24(2)6-5-10-16(31-24)9-14(27)19-20(29)11-7-12-17-18(22(11)30-21(10)19)13(26)8-15(28)23(17)32-25(12,3)4/h5-6,8-9,12,26-28H,7H2,1-4H3
InChIKey: OCZFLOUWXXGBPC-UHFFFAOYSA-N
DeepSMILES: OcccO)ccc6-coccC=CCOc6ccc%10c=O)c%14CC%18CO%21)C)C)))))))O)))))C)C
Scaffold Graph/Node/Bond level: O=c1c2c(oc3c4c(ccc13)OCC=C4)-c1cccc3c1C(CO3)C2
Scaffold Graph/Node level: OC1C2CCC3OCCCC3C2OC2C1CC1COC3CCCC2C13
Scaffold Graph level: CC1C2CCC3CCCCC3C2CC2C1CC1CCC3CCCC2C31
Functional groups: cO; coc; cC=CC; cOC; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
Cycloartobiloxanthone, cycloartobiloxanthone
External chemical identifiers:
CID:CID_10342859; ChEMBL:CHEMBL516519; ChEBI:CHEBI:169869
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cycloartobiloxanthone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 434.44
Log P RDKit 4.57
Topological polar surface area (Å2) RDKit 109.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 32
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 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
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 6
Cycloartobiloxanthone
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.48
Cycloartobiloxanthone
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 -6.07
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes