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

ID: ALA3746781

PubChem CID: 127042245

Max Phase: Preclinical

Molecular Formula: C22H23N3O6

Molecular Weight: 425.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H23N3O6/c1-22(2,13-31-12-19(26)27)25-11-16(15-6-4-5-7-17(15)25)20(28)21(29)24-14-8-9-18(30-3)23-10-14/h4-11H,12-13H2,1-3H3,(H,24,29)(H,26,27)

Standard InChI Key:  OSQGCCAHLDJEDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  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
    2.1825   -2.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1835   -3.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530   -5.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574   -2.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585   -3.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -6.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -7.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -7.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3247   -8.6128    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
 23 26  1  0
 23 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3746781

   ---

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: 425.44

Molecular Weight (Monoisotopic): 425.1587

AlogP: 2.70

#Rotatable Bonds: 9

Polar Surface Area: 119.75

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: 2.02

CX LogP: 2.50

CX LogD: -0.63

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.34

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