Biphenyl-4-yl(4-(1-hydroxycyclopentanecarbonyl)piperazin-1-yl)methanone

ID: ALA4447234

PubChem CID: 86275794

Max Phase: Preclinical

Molecular Formula: C23H26N2O3

Molecular Weight: 378.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2ccccc2)cc1)N1CCN(C(=O)C2(O)CCCC2)CC1

Standard InChI:  InChI=1S/C23H26N2O3/c26-21(20-10-8-19(9-11-20)18-6-2-1-3-7-18)24-14-16-25(17-15-24)22(27)23(28)12-4-5-13-23/h1-3,6-11,28H,4-5,12-17H2

Standard InChI Key:  SKKYHDJGXVGZHH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   37.7768   -4.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0311   -4.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3682   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7094   -4.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7836   -3.5948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7836   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4888   -4.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1941   -4.4120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.1941   -3.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4888   -3.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9012   -4.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9001   -5.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6095   -4.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3150   -4.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0228   -4.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0245   -3.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3124   -3.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6075   -3.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7322   -3.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4387   -3.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1460   -3.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1465   -2.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4339   -1.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7295   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0747   -3.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0723   -2.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6580   -3.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  6  7  1  0
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  7  8  1  0
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 23 24  1  0
 24 25  2  0
 25 20  1  0
  6 26  1  0
 26 27  2  0
 26  4  1  0
  4 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4447234

   [4-(1-Hydroxycyclopentanecarbonyl)piperazin-1-yl]-(4-phenylphenyl)methanone

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: 378.47

Molecular Weight (Monoisotopic): 378.1943

AlogP: 2.94

#Rotatable Bonds: 3

Polar Surface Area: 60.85

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.89

Np Likeness Score: -0.53

References

1. Martin MW, Lancia DR, Li H, Schiller SER, Toms AV, Wang Z, Bair KW, Castro J, Fessler S, Gotur D, Hubbs SE, Kauffman GS, Kershaw M, Luke GP, McKinnon C, Yao L, Lu W, Millan DS..  (2019)  Discovery and optimization of novel piperazines as potent inhibitors of fatty acid synthase (FASN).,  29  (8): [PMID:30803804] [10.1016/j.bmcl.2019.02.012]

Source

Source(1):

• Scientific Literature