IMPPAT Phytochemical information: 
Caloxanthone A

Caloxanthone A
Summary

SMILES: CC(=CCc1c(O)c(O)cc2c1oc1cc3OC(C)(C)C=Cc3c(c1c2=O)O)C
InChI: InChI=1S/C23H22O6/c1-11(2)5-6-13-19(25)15(24)9-14-21(27)18-17(28-22(13)14)10-16-12(20(18)26)7-8-23(3,4)29-16/h5,7-10,24-26H,6H2,1-4H3
InChIKey: PCBFLCFTJOTIAP-UHFFFAOYSA-N
DeepSMILES: CC=CCccO)cO)ccc6occcOCC)C)C=Cc6cc%10c%14=O)))O)))))))))))))))))))C
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2cc3c(cc12)C=CCO3
Scaffold Graph/Node level: OC1C2CCCCC2OC2CC3OCCCC3CC21
Scaffold Graph level: CC1C2CCCCC2CC2CC3CCCCC3CC21
Functional groups: CC=C(C)C; cO; coc; cOC; cC=CC; 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: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
caloxanthone a
External chemical identifiers:
CID:CID_10046140; ZINC:ZINC000013382721
Chemical structure download


Caloxanthone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.42
Log P RDKit 4.76
Topological polar surface area (Å2) RDKit 100.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
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 6
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 2
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 1
Number of aromatic rings RDKit 3
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


Caloxanthone 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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.32928


Caloxanthone 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 -4.94
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No