IMPPAT Phytochemical information: 
Clausenamide

Clausenamide
Summary

SMILES: O[C@@H]([C@H]1N(C)C(=O)[C@@H]([C@H]1c1ccccc1)O)c1ccccc1
InChI: InChI=1S/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3/t14-,15-,16+,17+/m0/s1
InChIKey: WGYGSZOQGYRGIP-MWDXBVQZSA-N
DeepSMILES: O[C@@H][C@H]NC)C=O)[C@@H][C@H]5cccccc6)))))))O)))))cccccc6
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)C(Cc2ccccc2)N1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)C(CC2CCCCC2)N1
Scaffold Graph level: CC1CC(CC2CCCCC2)C(C2CCCCC2)C1
Functional groups: CO; CN(C)C(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyrrolidines
ClassyFire Subclass: Phenylpyrrolidines
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
clausenamide
External chemical identifiers:
CID:CID_128412; ChEMBL:CHEMBL508970; ZINC:ZINC000005967137; SureChEMBL:SCHEMBL6369855
Chemical structure download


Clausenamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.35
Log P RDKit 1.71
Topological polar surface area (Å2) RDKit 60.77
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.28
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 2
Number of aromatic heterocycles RDKit 0
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


Clausenamide
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.906376


Clausenamide
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.02
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No