(4-(4-Ethylbenzoyl)piperidin-1-yl)(3-hydroxyphenyl)methanone

ID: ALA4474818

PubChem CID: 155537287

Max Phase: Preclinical

Molecular Formula: C21H23NO3

Molecular Weight: 337.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1ccc(C(=O)C2CCN(C(=O)c3cccc(O)c3)CC2)cc1

Standard InChI:  InChI=1S/C21H23NO3/c1-2-15-6-8-16(9-7-15)20(24)17-10-12-22(13-11-17)21(25)18-4-3-5-19(23)14-18/h3-9,14,17,23H,2,10-13H2,1H3

Standard InChI Key:  PFCFONBPOLDVJS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.3820  -22.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3808  -23.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0889  -23.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7985  -23.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7957  -22.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0871  -21.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5069  -23.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5082  -24.2317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2140  -23.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9206  -23.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6256  -23.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6285  -22.1941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9203  -21.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2092  -22.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3371  -21.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0440  -22.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3390  -20.9699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0373  -23.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7432  -23.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4528  -23.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4520  -22.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7455  -21.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7410  -24.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6742  -21.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9666  -22.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 19 23  1  0
  1 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474818

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.42

Molecular Weight (Monoisotopic): 337.1678

AlogP: 3.69

#Rotatable Bonds: 4

Polar Surface Area: 57.61

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.82

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.74

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -0.89

References

1. Granchi C, Lapillo M, Glasmacher S, Bononi G, Licari C, Poli G, El Boustani M, Caligiuri I, Rizzolio F, Gertsch J, Macchia M, Minutolo F, Tuccinardi T, Chicca A..  (2019)  Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor.,  62  (4): [PMID:30715876] [10.1021/acs.jmedchem.8b01483]

Source

Source(1):

• Scientific Literature