IMPPAT Phytochemical information: 
Echinacin
Echinacin
Summary

SMILES: O=C(OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m1/s1
InChIKey: WPQRDUGBKUNFJW-ZZSHFKPLSA-N
DeepSMILES: O=COC[C@H]O[C@@H]OcccO)ccc6)occc6=O)))cccccc6))O)))))))))))))[C@@H][C@H][C@@H]6O))O))O)))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CCCC(Oc2ccc3c(=O)cc(-c4ccccc4)oc3c2)O1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCC(OC2CCC3C(O)CC(C4CCCCC4)OC3C2)O1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCC(CC2CCC3C(C)CC(C4CCCCC4)CC3C2)C1
Functional groups: c/C=C/C(=O)OC; CO; cO[C@@H](C)OC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
Terniflorin, terniflorin, echinacin
External chemical identifiers:
CID:CID_6439941; ChEMBL:CHEMBL3597472; ZINC:ZINC000059731794; FDASRS:J64J7O64HY
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Echinacin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 578.53
Log P RDKit 2.02
Topological polar surface area (Å2) RDKit 196.35
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Echinacin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.138077
Echinacin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.29
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 No
P-glycoprotein substrate SwissADME No