IMPPAT Phytochemical information: 
(3R,4S)-3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one

(3R,4S)-3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one
Summary

SMILES: O=C1N(C)C=C([C@@H]([C@H]1O)c1ccccc1)c1ccccc1
InChI: InChI=1S/C18H17NO2/c1-19-12-15(13-8-4-2-5-9-13)16(17(20)18(19)21)14-10-6-3-7-11-14/h2-12,16-17,20H,1H3/t16-,17+/m0/s1
InChIKey: INMHUVDZWKKAOF-DLBZAZTESA-N
DeepSMILES: O=CNC)C=C[C@@H][C@H]6O))cccccc6)))))))cccccc6
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)C(c2ccccc2)=CN1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)C(C2CCCCC2)CN1
Scaffold Graph level: CC1CCC(C2CCCCC2)C(C2CCCCC2)C1
Functional groups: cC1=CN(C)C(=O)CC1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
homoclausenamide
External chemical identifiers:
CID:CID_24874130; ZINC:ZINC000000004773
Chemical structure download


(3R,4S)-3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 279.34
Log P RDKit 2.64
Topological polar surface area (Å2) RDKit 40.54
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 1
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


(3R,4S)-3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.92


(3R,4S)-3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.44
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