methyl 3-(4-(1H-indole-2-carboxamido)piperidin-1-yl)-3-oxopropanoate

ID: ALA4099919

PubChem CID: 137660719

Max Phase: Preclinical

Molecular Formula: C18H21N3O4

Molecular Weight: 343.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21N3O4/c1-25-17(23)11-16(22)21-8-6-13(7-9-21)19-18(24)15-10-12-4-2-3-5-14(12)20-15/h2-5,10,13,20H,6-9,11H2,1H3,(H,19,24)

Standard InChI Key:  GRUIVIDSWOQIOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.4764   -6.0189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2237   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1397   -7.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9328   -5.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9328   -5.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6378   -6.3491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7609   -5.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7609   -5.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0559   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3469   -5.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3469   -5.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0559   -4.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4700   -4.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4700   -3.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392   -7.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9286   -6.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1117   -6.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044   -7.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200   -8.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9355   -8.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1775   -5.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8854   -4.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5929   -5.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8858   -3.8982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5926   -5.9414    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  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099919

   ---

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: 1.45

#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: 13.14

CX Basic pKa: ┄

CX LogP: 0.36

CX LogD: 0.36

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -1.04

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