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

ID: ALA4098195

PubChem CID: 137661357

Max Phase: Preclinical

Molecular Formula: C18H21N3O4

Molecular Weight: 343.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N3O4/c22-16(5-6-17(23)24)21-9-7-13(8-10-21)19-18(25)15-11-12-3-1-2-4-14(12)20-15/h1-4,11,13,20H,5-10H2,(H,19,25)(H,23,24)

Standard InChI Key:  JPBFIOZSQIURDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.5808   -5.0531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -5.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441   -6.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0372   -4.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0372   -4.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7422   -5.3834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8653   -4.1576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8653   -4.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1603   -5.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4512   -4.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4512   -4.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1603   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5744   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5744   -2.9318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4435   -6.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330   -5.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161   -5.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8088   -6.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2244   -7.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399   -7.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2819   -4.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9898   -3.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6973   -4.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4052   -3.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6970   -4.9757    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
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098195

   ---

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: 343.38

Molecular Weight (Monoisotopic): 343.1532

AlogP: 1.75

#Rotatable Bonds: 5

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: 4.44

CX Basic pKa: ┄

CX LogP: 0.14

CX LogD: -2.71

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -1.12

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