IMPPAT Phytochemical information: 
N-desmethylequisetin
N-desmethylequisetin
Summary

SMILES: C/C=C/[C@@H]1C=C[C@H]2[C@H]([C@]1(C)/C(=C\1/C(=O)N[C@H](C1=O)CO)/O)CC[C@H](C2)C
InChI: InChI=1S/C21H29NO4/c1-4-5-14-8-7-13-10-12(2)6-9-15(13)21(14,3)19(25)17-18(24)16(11-23)22-20(17)26/h4-5,7-8,12-16,23,25H,6,9-11H2,1-3H3,(H,22,26)/b5-4+,19-17-/t12-,13-,14-,15-,16+,21-/m1/s1
InChIKey: TYCWBBBQIATAJE-GEZPOGBYSA-N
DeepSMILES: C/C=C/[C@@H]C=C[C@H][C@H][C@]6C)/C=C/C=O)N[C@H]C/5=O))CO))))))/O)))CC[C@H]C6)C
Scaffold Graph/Node/Bond level: O=C1CNC(=O)C1=CC1CC=CC2CCCCC12
Scaffold Graph/Node level: OC1CNC(O)C1CC1CCCC2CCCCC21
Scaffold Graph level: CC1CCC(C)C1CC1CCCC2CCCCC21
Functional groups: C/C=C/C; CC=CC; C/C(O)=C1\C(=O)CNC1=O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyrrolidines
ClassyFire Subclass: Pyrrolidones
NP Classifier Biosynthetic pathway: Amino acids and Peptides|Polyketides
NP Classifier Superclass: Cyclic polyketides
NP Classifier Class: 3-Decalinoyltetramic acids
Synonymous chemical names:
trichosetin
External chemical identifiers:
CID:CID_91819764; ChEBI:CHEBI:142133
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N-desmethylequisetin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 359.47
Log P RDKit 2.68
Topological polar surface area (Å2) RDKit 86.63
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
N-desmethylequisetin
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 0.312908
N-desmethylequisetin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.29
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes