(1-(2-Fluoro-5-hydroxybenzoyl)piperidin-4-yl)(4-isopropylphenyl)methanone

ID: ALA4536045

Cas Number: 2324160-91-8

PubChem CID: 138319671

Product Number: M651730, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H24FNO3

Molecular Weight: 369.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(C(=O)C2CCN(C(=O)c3cc(O)ccc3F)CC2)cc1

Standard InChI:  InChI=1S/C22H24FNO3/c1-14(2)15-3-5-16(6-4-15)21(26)17-9-11-24(12-10-17)22(27)19-13-18(25)7-8-20(19)23/h3-8,13-14,17,25H,9-12H2,1-2H3

Standard InChI Key:  WUUBZNFATQKRPH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.9412  -14.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6509  -14.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481  -13.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394  -13.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3592  -14.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3605  -15.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0663  -14.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730  -14.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4780  -14.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4809  -13.7705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7727  -13.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0616  -13.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1895  -13.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8963  -13.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1913  -12.5462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8896  -14.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5956  -15.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3052  -14.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3044  -13.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5978  -13.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5934  -15.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332  -14.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2328  -13.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5960  -12.5488    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5248  -13.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242  -12.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174  -13.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 23  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 17 21  1  0
 22 23  2  0
 20 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536045

   MAGL-IN-1

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: 369.44

Molecular Weight (Monoisotopic): 369.1740

AlogP: 4.39

#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: 8.63

CX Basic pKa: ┄

CX LogP: 4.18

CX LogD: 4.16

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: -1.06

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]

2. Granchi C,Bononi G,Ferrisi R,Gori E,Mantini G,Glasmacher S,Poli G,Palazzolo S,Caligiuri I,Rizzolio F,Canzonieri V,Perin T,Gertsch J,Sodi A,Giovannetti E,Macchia M,Minutolo F,Tuccinardi T,Chicca A.  (2021)  Design, synthesis and biological evaluation of second-generation benzoylpiperidine derivatives as reversible monoacylglycerol lipase (MAGL) inhibitors.,  209  [PMID:33045662] [10.1016/j.ejmech.2020.112857]

3. Hoover, Heather S; Blankman, Jacqueline L; Niessen, Sherry and Cravatt, Benjamin F.  2008-11-15  Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.  [PMID:18657971]

4. Ogasawara, Daisuke and 6 more authors.  2019-02-14  Discovery and Optimization of Selective and in Vivo Active Inhibitors of the Lysophosphatidylserine Lipase α/β-Hydrolase Domain-Containing 12 (ABHD12).  [PMID:30720278]

5. Arena, Chiara and 21 more authors.  2020-12-15  The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis.  [PMID:33002735]

Source

Source(1):

• Scientific Literature