(1-(3-Bromo-5-hydroxybenzoyl)piperidin-4-yl)(4-chlorophenyl)-methanone

ID: ALA4530498

PubChem CID: 155545776

Max Phase: Preclinical

Molecular Formula: C19H17BrClNO3

Molecular Weight: 422.71

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(Cl)cc1)C1CCN(C(=O)c2cc(O)cc(Br)c2)CC1

Standard InChI:  InChI=1S/C19H17BrClNO3/c20-15-9-14(10-17(23)11-15)19(25)22-7-5-13(6-8-22)18(24)12-1-3-16(21)4-2-12/h1-4,9-11,13,23H,5-8H2

Standard InChI Key:  ZXYNOWGZGQBJTP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   23.2184   -8.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2172   -9.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9253  -10.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6349   -9.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6321   -8.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9235   -8.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5106   -8.3949    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.3433  -10.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3446  -10.8471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0503   -9.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7570  -10.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4620   -9.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4649   -8.8095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7567   -8.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0456   -8.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1735   -8.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8803   -8.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1754   -7.5853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8737   -9.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5796  -10.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2892   -9.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2884   -8.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5819   -8.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5774  -10.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9956   -8.4019    0.0000 Br  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
  1  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 20 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4530498

   ---

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: 422.71

Molecular Weight (Monoisotopic): 421.0080

AlogP: 4.54

#Rotatable Bonds: 3

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: 8.16

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.04

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