methyl 4-(4-(1H-indole-2-carboxamido)piperidine-1-carbonyl)benzoate

ID: ALA4104277

PubChem CID: 137657769

Max Phase: Preclinical

Molecular Formula: C23H23N3O4

Molecular Weight: 405.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(C(=O)N2CCC(NC(=O)c3cc4ccccc4[nH]3)CC2)cc1

Standard InChI:  InChI=1S/C23H23N3O4/c1-30-23(29)16-8-6-15(7-9-16)22(28)26-12-10-18(11-13-26)24-21(27)20-14-17-4-2-3-5-19(17)25-20/h2-9,14,18,25H,10-13H2,1H3,(H,24,27)

Standard InChI Key:  DBRZDYJXCYHSQZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.3101   -6.8567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0574   -7.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -8.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7665   -6.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7665   -5.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4715   -7.1870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946   -5.9612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946   -6.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8896   -7.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1806   -6.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1806   -5.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8896   -5.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3037   -5.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3037   -4.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1729   -8.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7623   -7.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9454   -7.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381   -8.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -8.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7692   -8.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0112   -5.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0071   -6.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7138   -7.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4227   -6.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4204   -5.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7131   -5.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1327   -7.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1335   -8.0033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8401   -6.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8416   -8.4112    0.0000 C   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  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  1  0
 27 29  2  0
 24 27  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104277

   ---

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: 405.45

Molecular Weight (Monoisotopic): 405.1689

AlogP: 2.99

#Rotatable Bonds: 4

Polar Surface Area: 91.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.15

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