2-Amino-1-(3-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)-1H-pyrrolo[2,3-b]quinoxaline-3-carboxamide

ID: ALA3321808

PubChem CID: 118387079

Max Phase: Preclinical

Molecular Formula: C20H16N8O

Molecular Weight: 384.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc(-c2cccc(-n3c(N)c(C(N)=O)c4nc5ccccc5nc43)c2)[nH]1

Standard InChI:  InChI=1S/C20H16N8O/c1-10-23-19(27-26-10)11-5-4-6-12(9-11)28-17(21)15(18(22)29)16-20(28)25-14-8-3-2-7-13(14)24-16/h2-9H,21H2,1H3,(H2,22,29)(H,23,26,27)

Standard InChI Key:  KEHIAIYAOIMYGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    4.6215  -17.3826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292  -16.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292  -16.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6215  -15.7482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138  -16.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061  -15.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983  -16.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983  -16.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061  -17.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138  -16.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064  -17.2265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064  -15.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5867  -16.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3589  -15.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121  -14.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1483  -14.9156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3589  -18.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8121  -18.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646  -19.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8640  -19.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4108  -18.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1582  -18.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039  -16.5654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2101  -19.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5454  -19.8647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3581  -19.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5280  -18.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8203  -18.5714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2746  -18.6474    0.0000 C   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  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3321808

   2-amino-1-[3-(5-methyl-1H-1,2,4-triazol-3-yl)phenyl]pyrrolo[3,2-b]quinoxaline-3-carboxamide

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: 384.40

Molecular Weight (Monoisotopic): 384.1447

AlogP: 2.35

#Rotatable Bonds: 3

Polar Surface Area: 141.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.53

CX Basic pKa: 3.01

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.40

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