2-amino-7-bromo-1-(3-hydroxy-2,6-dimethylphenyl)-1H-pyrrolo[2,3-b]quinoxaline-3-carboxamide

ID: ALA5195417

PubChem CID: 168286690

Max Phase: Preclinical

Molecular Formula: C19H16BrN5O2

Molecular Weight: 426.27

Names and Identifiers

Canonical SMILES:  Cc1ccc(O)c(C)c1-n1c(N)c(C(N)=O)c2nc3ccc(Br)cc3nc21

Standard InChI:  InChI=1S/C19H16BrN5O2/c1-8-3-6-13(26)9(2)16(8)25-17(21)14(18(22)27)15-19(25)24-12-7-10(20)4-5-11(12)23-15/h3-7,26H,21H2,1-2H3,(H2,22,27)

Standard InChI Key:  JJCCADQSMGTNJK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -1.3192   -2.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5242   -2.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -1.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448   -0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295   -0.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    0.4880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    0.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    1.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601    2.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601    2.8007    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754    1.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754    0.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601    0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8601   -0.3379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -0.8902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9924   -0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1853    0.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7067    0.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9780    0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1343    0.9600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5754   -0.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800   -1.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874   -1.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309   -1.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1518   -1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785   -2.2170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707   -2.0360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  4  3  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  8  7  1  0
  9  8  2  0
  9 10  1  0
 11  9  1  0
 12 11  2  0
 13 12  1  0
  7 13  2  0
 13 14  1  0
 14  4  2  0
 15  5  1  0
 15 16  1  0
 17 16  1  0
 17 18  1  0
 19 17  2  0
 19 20  1  0
 21 19  1  0
 22 21  2  0
 23 22  1  0
 16 23  2  0
 23 24  1  0
 25 15  1  0
  3 25  2  0
 25 26  1  0
 27  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5195417

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 426.27

Molecular Weight (Monoisotopic): 425.0487

AlogP: 3.34

#Rotatable Bonds: 2

Polar Surface Area: 120.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.76

CX Basic pKa: 0.18

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -0.93

References

1. Szychowski J, Papp R, Dietrich E, Liu B, Vallée F, Leclaire ME, Fourtounis J, Martino G, Perryman AL, Pau V, Yin SY, Mader P, Roulston A, Truchon JF, Marshall CG, Diallo M, Duffy NM, Stocco R, Godbout C, Bonneau-Fortin A, Kryczka R, Bhaskaran V, Mao D, Orlicky S, Beaulieu P, Turcotte P, Kurinov I, Sicheri F, Mamane Y, Gallant M, Black WC..  (2022)  Discovery of an Orally Bioavailable and Selective PKMYT1 Inhibitor, RP-6306.,  65  (15.0): [PMID:35880755] [10.1021/acs.jmedchem.2c00552]

Source

Source(1):

• Scientific Literature