3-(3-(2-(6-Methoxypyridin-3-ylamino)-2-oxoacetyl)-1H-indol-1-yl)propanoic acid

ID: ALA3746300

PubChem CID: 127042247

Max Phase: Preclinical

Molecular Formula: C19H17N3O5

Molecular Weight: 367.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)C(=O)c2cn(CCC(=O)O)c3ccccc23)cn1

Standard InChI:  InChI=1S/C19H17N3O5/c1-27-16-7-6-12(10-20-16)21-19(26)18(25)14-11-22(9-8-17(23)24)15-5-3-2-4-13(14)15/h2-7,10-11H,8-9H2,1H3,(H,21,26)(H,23,24)

Standard InChI Key:  WQQIRBDPWCMEFL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808    3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505    2.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0571    6.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5257    6.3996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5244    5.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0544    3.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5858    3.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9944    5.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7921    4.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3299   -5.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -4.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  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
 18 21  1  0
 21 22  1  0
  7 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3746300

   ---

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: 367.36

Molecular Weight (Monoisotopic): 367.1168

AlogP: 2.34

#Rotatable Bonds: 7

Polar Surface Area: 110.52

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.05

CX Basic pKa: 2.02

CX LogP: 2.18

CX LogD: -0.95

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -1.72

References

1. Colley HE, Muthana M, Danson SJ, Jackson LV, Brett ML, Harrison J, Coole SF, Mason DP, Jennings LR, Wong M, Tulasi V, Norman D, Lockey PM, Williams L, Dossetter AG, Griffen EJ, Thompson MJ..  (2015)  An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer.,  58  (23): [PMID:26580420] [10.1021/acs.jmedchem.5b01312]

Source

Source(1):

• Scientific Literature