2-Amino-1-(3-hydroxyphenyl)-1H-pyrrolo[2,3-b]quinoxaline-3-carboxamide

ID: ALA3321807

PubChem CID: 118709761

Max Phase: Preclinical

Molecular Formula: C17H13N5O2

Molecular Weight: 319.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(N)n(-c2cccc(O)c2)c2nc3ccccc3nc12

Standard InChI:  InChI=1S/C17H13N5O2/c18-15-13(16(19)24)14-17(21-12-7-2-1-6-11(12)20-14)22(15)9-4-3-5-10(23)8-9/h1-8,23H,18H2,(H2,19,24)

Standard InChI Key:  WZMDHRTURUZPDL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.0705  -22.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7782  -21.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7782  -21.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705  -20.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628  -21.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551  -20.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474  -21.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474  -21.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551  -22.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3628  -21.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554  -22.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5554  -20.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0357  -21.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8079  -20.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611  -19.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5973  -19.8472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8079  -22.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611  -23.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5136  -24.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3130  -24.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8639  -23.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6073  -23.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8529  -21.5012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6633  -24.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 12 13  2  0
 11 13  1  0
  2 11  1  0
  3 12  1  0
 14 15  2  0
 14 16  1  0
 12 14  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 11 17  1  0
 13 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3321807

   ---

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: 319.32

Molecular Weight (Monoisotopic): 319.1069

AlogP: 1.96

#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: 10.02

CX Basic pKa: 1.00

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -1.06

References

1. Unzue A, Dong J, Lafleur K, Zhao H, Frugier E, Caflisch A, Nevado C..  (2014)  Pyrrolo[3,2-b]quinoxaline derivatives as types I1/2 and II Eph tyrosine kinase inhibitors: structure-based design, synthesis, and in vivo validation.,  57  (15): [PMID:25076195] [10.1021/jm5009242]

2. 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