IMPPAT Phytochemical information: 
Canescin A
Canescin A
Summary

SMILES: CO[C@@H]1C[C@H](OC1=O)c1c(O)cc2c(c1O)c(=O)oc(c2)C
InChI: InChI=1S/C15H14O7/c1-6-3-7-4-8(16)12(13(17)11(7)15(19)21-6)9-5-10(20-2)14(18)22-9/h3-4,9-10,16-17H,5H2,1-2H3/t9-,10+/m0/s1
InChIKey: RIGNEELUCYJHBN-VHSXEESVSA-N
DeepSMILES: CO[C@@H]C[C@H]OC5=O)))ccO)cccc6O))c=O)occ6)C
Scaffold Graph/Node/Bond level: O=C1CCC(c2ccc3ccoc(=O)c3c2)O1
Scaffold Graph/Node level: OC1CCC(C2CCC3CCOC(O)C3C2)O1
Scaffold Graph level: CC1CCC(C2CCC3CCCC(C)C3C2)C1
Functional groups: COC; COC(=O)C; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isocoumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Isocoumarins
Synonymous chemical names:
canescin
External chemical identifiers:
CID:CID_90470500; ZINC:ZINC000013382947
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Canescin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 306.27
Log P RDKit 1.52
Topological polar surface area (Å2) RDKit 106.2
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.33
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 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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
Canescin 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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.809931
Canescin 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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.82
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No