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

ID: ALA3321820

PubChem CID: 118709764

Max Phase: Preclinical

Molecular Formula: C21H19N7O2

Molecular Weight: 401.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H19N7O2/c22-18-16(19(23)29)17-20(27-15-7-2-1-6-14(15)26-17)28(18)13-5-3-4-12(10-13)25-21(30)24-11-8-9-11/h1-7,10-11H,8-9,22H2,(H2,23,29)(H2,24,25,30)

Standard InChI Key:  XJPBPKXDLBGCMY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.6967   -2.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9823   -1.1362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -1.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1639   -1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1639   -2.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -2.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -2.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4814   -2.6287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9664   -1.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844    0.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332   -0.2956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -3.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844   -4.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393   -4.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -4.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7982   -4.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433   -3.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -1.9612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053   -4.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8602   -5.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6671   -5.4972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -5.9386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9221   -6.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536   -7.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5382   -6.8330    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  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 29 28  1  0
 30 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3321820

   ---

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: 401.43

Molecular Weight (Monoisotopic): 401.1600

AlogP: 2.54

#Rotatable Bonds: 4

Polar Surface Area: 140.95

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.25

CX Basic pKa: 1.01

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -1.82

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