IMPPAT Phytochemical information: 
Calophyllic acid
Calophyllic acid
Summary

SMILES: OC(=O)/C=C(\c1c2OC(C)(C)C=Cc2c2c(c1O)C(=O)C(C(O2)C)C)/c1ccccc1
InChI: InChI=1S/C25H24O6/c1-13-14(2)30-23-16-10-11-25(3,4)31-24(16)19(22(29)20(23)21(13)28)17(12-18(26)27)15-8-6-5-7-9-15/h5-14,29H,1-4H3,(H,26,27)/b17-12-
InChIKey: SSJOJPHKKKSPGS-ATVHPVEESA-N
DeepSMILES: OC=O)/C=C\ccOCC)C)C=Cc6ccc%10O))C=O)CCO6)C))C))))))))))))/cccccc6
Scaffold Graph/Node/Bond level: C=C(c1ccccc1)c1cc2c(c3c1OCC=C3)OCCC2=O
Scaffold Graph/Node level: CC(C1CCCCC1)C1CC2C(O)CCOC2C2CCCOC12
Scaffold Graph level: CC1CCCC2C1CC(C(C)C1CCCCC1)C1CCCCC21
Functional groups: c/C(c)=C\C(=O)O; cOC; cC=CC; cO; cC(=O)C
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: Coumarins
NP Classifier Class: Pyranocoumarins
Synonymous chemical names:
calophyllic, calophyllic acid
External chemical identifiers:
CID:CID_44257564; SureChEMBL:SCHEMBL7126875
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Calophyllic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 420.46
Log P RDKit 4.69
Topological polar surface area (Å2) RDKit 93.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.28
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Calophyllic acid
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 0.7
Calophyllic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -5.07
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No