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

ID: ALA4282040

Chembl Id: CHEMBL4282040

PubChem CID: 132941103

Max Phase: Preclinical

Molecular Formula: C19H18ClNO3

Molecular Weight: 343.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(Cl)cc1)C1CCN(C(=O)c2cccc(O)c2)CC1

Standard InChI:  InChI=1S/C19H18ClNO3/c20-16-6-4-13(5-7-16)18(23)14-8-10-21(11-9-14)19(24)15-2-1-3-17(22)12-15/h1-7,12,14,22H,8-11H2

Standard InChI Key:  XSAQFVZJTOJQCI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4282040

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 343.81

Molecular Weight (Monoisotopic): 343.0975

AlogP: 3.78

#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: 8.82

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -1.03

References

1. Bononi G, Granchi C, Lapillo M, Giannotti M, Nieri D, Fortunato S, Boustani ME, Caligiuri I, Poli G, Carlson KE, Kim SH, Macchia M, Martinelli A, Rizzolio F, Chicca A, Katzenellenbogen JA, Minutolo F, Tuccinardi T..  (2018)  Discovery of long-chain salicylketoxime derivatives as monoacylglycerol lipase (MAGL) inhibitors.,  157  [PMID:30144699] [10.1016/j.ejmech.2018.08.038]

2. 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]

3. Granchi C,Rizzolio F,Palazzolo S,Carmignani S,Macchia M,Saccomanni G,Manera C,Martinelli A,Minutolo F,Tuccinardi T.  (2016)  Structural Optimization of 4-Chlorobenzoylpiperidine Derivatives for the Development of Potent, Reversible, and Selective Monoacylglycerol Lipase (MAGL) Inhibitors.,  59  (22): [PMID:27809504] [10.1021/acs.jmedchem.6b01459]

4. Bononi G, Tonarini G, Poli G, Barravecchia I, Caligiuri I, Macchia M, Rizzolio F, Demontis GC, Minutolo F, Granchi C, Tuccinardi T..  (2021)  Monoacylglycerol lipase (MAGL) inhibitors based on a diphenylsulfide-benzoylpiperidine scaffold.,  223  [PMID:34218085] [10.1016/j.ejmech.2021.113679]

Source

Source(1):

• Scientific Literature