IMPPAT Phytochemical information: 
Equisetumpyrone
Equisetumpyrone
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c(O)cc(oc2=O)/C=C/c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C19H20O11/c20-7-13-14(24)15(25)16(26)19(29-13)30-17-12(23)6-9(28-18(17)27)3-1-8-2-4-10(21)11(22)5-8/h1-6,13-16,19-26H,7H2/b3-1+/t13-,14-,15+,16-,19+/m1/s1
InChIKey: WDIZWIYNWPPECY-PMSYKMBQSA-N
DeepSMILES: OC[C@H]O[C@@H]OccO)ccoc6=O)))/C=C/cccccc6)O))O))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1oc(C=Cc2ccccc2)ccc1OC1CCCCO1
Scaffold Graph/Node level: OC1OC(CCC2CCCCC2)CCC1OC1CCCCO1
Scaffold Graph level: CC1CC(CCC2CCCCC2)CCC1CC1CCCCC1
Functional groups: CO; cO[C@@H](C)OC; cO; coc; c=O; c/C=C/c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Styrylpyrones
NP Classifier Class: Kavalactones and derivatives
Synonymous chemical names:
Equisetumpyrone, equisetumpyrone
External chemical identifiers:
CID:CID_102247460; ZINC:ZINC000238745510
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Equisetumpyrone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.36
Log P RDKit -0.89
Topological polar surface area (Å2) RDKit 190.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 5
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
Equisetumpyrone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
Equisetumpyrone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.06
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
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