(2'-chloro-4'-methoxybiphenyl-4-yl)(4-(1-hydroxycyclopropanecarbonyl)piperazin-1-yl)methanone

ID: ALA4455553

PubChem CID: 86272922

Max Phase: Preclinical

Molecular Formula: C22H23ClN2O4

Molecular Weight: 414.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccc(C(=O)N3CCN(C(=O)C4(O)CC4)CC3)cc2)c(Cl)c1

Standard InChI:  InChI=1S/C22H23ClN2O4/c1-29-17-6-7-18(19(23)14-17)15-2-4-16(5-3-15)20(26)24-10-12-25(13-11-24)21(27)22(28)8-9-22/h2-7,14,28H,8-13H2,1H3

Standard InChI Key:  BDRSMBBEDKDLAN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   26.4390  -16.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2562  -16.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8476  -15.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2633  -15.5101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2633  -16.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9685  -16.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6738  -16.3273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6738  -15.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9685  -15.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3809  -16.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3797  -17.5541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0892  -16.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7947  -16.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5025  -16.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5042  -15.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7921  -15.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0872  -15.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2119  -15.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9184  -15.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6257  -15.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6262  -14.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9136  -13.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2092  -14.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5544  -15.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5520  -14.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1377  -15.0974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5001  -13.8874    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.3334  -13.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0416  -14.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  4 24  1  0
 24 25  2  0
 24  3  1  0
  3 26  1  0
 23 27  1  0
 21 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4455553

   [4-(2-Chloro-4-methoxyphenyl)phenyl]-[4-(1-hydroxycyclopropanecarbonyl)piperazin-1-yl]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: 414.89

Molecular Weight (Monoisotopic): 414.1346

AlogP: 2.82

#Rotatable Bonds: 4

Polar Surface Area: 70.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: ┄

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.83

Np Likeness Score: -0.65

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