4-(4-(N-benzyl-1H-indole-2-carboxamido)piperidin-1-yl)-4-oxobutanoic acid

ID: ALA4095762

PubChem CID: 137653381

Max Phase: Preclinical

Molecular Formula: C25H27N3O4

Molecular Weight: 433.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCC(=O)N1CCC(N(Cc2ccccc2)C(=O)c2cc3ccccc3[nH]2)CC1

Standard InChI:  InChI=1S/C25H27N3O4/c29-23(10-11-24(30)31)27-14-12-20(13-15-27)28(17-18-6-2-1-3-7-18)25(32)22-16-19-8-4-5-9-21(19)26-22/h1-9,16,20,26H,10-15,17H2,(H,30,31)

Standard InChI Key:  QQHCYBDHGROFJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   11.9342   -6.9063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0573   -5.6805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0573   -6.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3524   -6.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6433   -6.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6433   -5.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3524   -5.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7664   -5.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7664   -4.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4740   -5.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2268   -6.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9335   -7.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6409   -8.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5188   -6.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2275   -5.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7751   -6.5736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4352   -7.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6358   -7.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2297   -7.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4152   -7.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0057   -7.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167   -8.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2299   -8.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1819   -5.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8894   -5.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5973   -5.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8890   -6.4986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6383   -8.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3448   -9.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0538   -8.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0519   -8.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3448   -7.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  7  1  0
  8  9  2  0
  2  8  1  0
  1  5  1  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
 12 13  1  0
 11 14  1  0
 11 15  2  0
 14 16  1  0
 16 19  1  0
 18 17  1  0
 17 14  2  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
 10 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 13 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095762

   ---

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: 433.51

Molecular Weight (Monoisotopic): 433.2002

AlogP: 3.67

#Rotatable Bonds: 7

Polar Surface Area: 93.71

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.29

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: -0.87

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -1.30

References

1. Jukič M, Ilaš J, Brvar M, Kikelj D, Cesar J, Anderluh M..  (2017)  Linker-switch approach towards new ATP binding site inhibitors of DNA gyrase B.,  125  [PMID:27689732] [10.1016/j.ejmech.2016.09.040]

Source

Source(1):

• Scientific Literature