(Z)-3-(4-(2-benzylpiperidin-1-yl)-4-oxobut-2-enamido)benzamide

ID: ALA4093441

PubChem CID: 137655632

Max Phase: Preclinical

Molecular Formula: C23H25N3O3

Molecular Weight: 391.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cccc(NC(=O)/C=C\C(=O)N2CCCCC2Cc2ccccc2)c1

Standard InChI:  InChI=1S/C23H25N3O3/c24-23(29)18-9-6-10-19(16-18)25-21(27)12-13-22(28)26-14-5-4-11-20(26)15-17-7-2-1-3-8-17/h1-3,6-10,12-13,16,20H,4-5,11,14-15H2,(H2,24,29)(H,25,27)/b13-12-

Standard InChI Key:  PYVZAYARZDPDGX-SEYXRHQNSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    8.6080   -2.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6068   -3.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3149   -3.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0245   -3.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0217   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3131   -2.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7279   -2.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4371   -2.4096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7248   -1.1865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3147   -4.4642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6069   -4.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6067   -5.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3143   -6.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0221   -5.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7297   -6.0989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0223   -4.8730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8993   -4.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7242   -6.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4278   -7.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1380   -6.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1401   -6.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4321   -5.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4308   -4.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1379   -4.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8443   -4.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5509   -4.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5501   -3.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8368   -3.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1331   -3.6455    0.0000 C   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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 11 17  2  0
 15 18  1  0
 15 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093441

   ---

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: 391.47

Molecular Weight (Monoisotopic): 391.1896

AlogP: 2.90

#Rotatable Bonds: 6

Polar Surface Area: 92.50

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.85

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -1.00

References

1. Upton K, Meyers M, Thorsell AG, Karlberg T, Holechek J, Lease R, Schey G, Wolf E, Lucente A, Schüler H, Ferraris D..  (2017)  Design and synthesis of potent inhibitors of the mono(ADP-ribosyl)transferase, PARP14.,  27  (13): [PMID:28495083] [10.1016/j.bmcl.2017.04.089]

Source

Source(1):

• Scientific Literature