2-amino-1-(3-(cyclopropylcarbamoyl)phenyl)-1H-pyrrolo[2,3-b]quinoxaline-3-carboxamide

ID: ALA3321815

PubChem CID: 118709763

Max Phase: Preclinical

Molecular Formula: C21H18N6O2

Molecular Weight: 386.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(N)n(-c2cccc(C(=O)NC3CC3)c2)c2nc3ccccc3nc12

Standard InChI:  InChI=1S/C21H18N6O2/c22-18-16(19(23)28)17-20(26-15-7-2-1-6-14(15)25-17)27(18)13-5-3-4-11(10-13)21(29)24-12-8-9-12/h1-7,10,12H,8-9,22H2,(H2,23,28)(H,24,29)

Standard InChI Key:  BJZQEYHAHMGINT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    1.7490   -2.6279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4634   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4634   -1.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490   -0.9779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0345   -1.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3200   -0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -1.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3200   -2.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0345   -2.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2480   -2.4703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2480   -1.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7330   -1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5030   -0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999   -0.1373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5030   -3.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509   -3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -4.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0129   -4.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649   -4.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100   -3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579   -1.8029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3718   -4.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269   -5.1672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4338   -5.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0474   -5.8894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2189   -5.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9239   -3.7695    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
 24 25  1  0
 25 26  1  0
 27 26  1  0
 28 27  1  0
 26 28  1  0
 24 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3321815

   ---

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: 386.42

Molecular Weight (Monoisotopic): 386.1491

AlogP: 2.15

#Rotatable Bonds: 4

Polar Surface Area: 128.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.92

CX Basic pKa: 1.01

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.57

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]

Source

Source(1):

• Scientific Literature