3-(4-(1H-indole-2-carboxamido)piperidin-1-yl)-3-oxopropanoic acid

ID: ALA4090385

PubChem CID: 137644008

Max Phase: Preclinical

Molecular Formula: C17H19N3O4

Molecular Weight: 329.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC(=O)N1CCC(NC(=O)c2cc3ccccc3[nH]2)CC1

Standard InChI:  InChI=1S/C17H19N3O4/c21-15(10-16(22)23)20-7-5-12(6-8-20)18-17(24)14-9-11-3-1-2-4-13(11)19-14/h1-4,9,12,19H,5-8,10H2,(H,18,24)(H,22,23)

Standard InChI Key:  GJGBAUUSRRVJKH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.1050   -6.1097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8523   -6.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7682   -7.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5613   -6.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5613   -5.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2663   -6.4399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3895   -5.2141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3895   -6.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6845   -6.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9754   -6.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9754   -5.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6845   -4.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0985   -4.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0985   -3.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677   -7.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -6.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -6.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3329   -7.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485   -8.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5641   -8.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8061   -5.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5140   -4.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2215   -5.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5143   -3.9890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 15  1  0
  1 16  1  0
  4  5  2  0
  4  6  1  0
  2  4  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 12  1  0
 13 14  2  0
  7 13  1  0
  6 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090385

   ---

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: 329.36

Molecular Weight (Monoisotopic): 329.1376

AlogP: 1.36

#Rotatable Bonds: 4

Polar Surface Area: 102.50

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 0.21

CX LogD: -3.04

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -0.95

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