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

ID: ALA4088040

PubChem CID: 137643919

Max Phase: Preclinical

Molecular Formula: C21H25N3O4

Molecular Weight: 383.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN(C(=O)c1cc2ccccc2[nH]1)C1CCN(C(=O)CCC(=O)O)CC1

Standard InChI:  InChI=1S/C21H25N3O4/c1-2-11-24(21(28)18-14-15-5-3-4-6-17(15)22-18)16-9-12-23(13-10-16)19(25)7-8-20(26)27/h2-6,14,16,22H,1,7-13H2,(H,26,27)

Standard InChI Key:  QWHVGOJZRRVGMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  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
   12.6402   -8.9499    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
  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
 13 14  2  0
 11 15  1  0
 11 16  2  0
 15 17  1  0
 17 20  1  0
 19 18  1  0
 18 15  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 10 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088040

   ---

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: 383.45

Molecular Weight (Monoisotopic): 383.1845

AlogP: 2.65

#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: 1.10

CX LogD: -1.87

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -1.29

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