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

ID: ALA5194389

PubChem CID: 168288841

Max Phase: Preclinical

Molecular Formula: C25H25NO3

Molecular Weight: 387.48

Names and Identifiers

Canonical SMILES:  O=C(c1cccc(O)c1)N1CCC(Cc2cccc(Oc3ccccc3)c2)CC1

Standard InChI:  InChI=1S/C25H25NO3/c27-22-8-5-7-21(18-22)25(28)26-14-12-19(13-15-26)16-20-6-4-11-24(17-20)29-23-9-2-1-3-10-23/h1-11,17-19,27H,12-16H2

Standard InChI Key:  XNDGXGMGLPQQBA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -2.1342    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -0.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225   -0.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081   -0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109    0.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243    0.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481   -0.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5602   -0.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5550    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2664    0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802    0.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9782   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2663   -0.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -0.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244   -0.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1341   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370    0.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4241    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504    0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620    0.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.6460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2658   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9802   -0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9794    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680    0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636   -1.6460    0.0000 O   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
  2  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5194389

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 387.48

Molecular Weight (Monoisotopic): 387.1834

AlogP: 5.28

#Rotatable Bonds: 5

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.82

CX Basic pKa: ┄

CX LogP: 5.18

CX LogD: 5.17

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.58

References

1. Bononi G, Di Stefano M, Poli G, Ortore G, Meier P, Masetto F, Caligiuri I, Rizzolio F, Macchia M, Chicca A, Avan A, Giovannetti E, Vagaggini C, Brai A, Dreassi E, Valoti M, Minutolo F, Granchi C, Gertsch J, Tuccinardi T..  (2022)  Reversible Monoacylglycerol Lipase Inhibitors: Discovery of a New Class of Benzylpiperidine Derivatives.,  65  (10.0): [PMID:35522977] [10.1021/acs.jmedchem.1c01806]

Source

Source(1):

• Scientific Literature