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

ID: ALA3321810

PubChem CID: 118709762

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(NC(=O)C3CC3)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)13-5-3-4-12(10-13)24-21(29)11-8-9-11/h1-7,10-11H,8-9,22H2,(H2,23,28)(H,24,29)

Standard InChI Key:  AGFAHKSTBACDOB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    2.8864  -15.4862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010  -15.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010  -14.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864  -13.8362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720  -14.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575  -13.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430  -14.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430  -15.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575  -15.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720  -15.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856  -15.3288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856  -13.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705  -14.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6405  -13.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0885  -12.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4374  -12.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6405  -16.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0885  -16.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3434  -17.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1504  -17.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7024  -17.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4475  -16.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955  -14.6612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094  -17.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7644  -18.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5713  -18.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2123  -18.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1850  -18.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3565  -17.9409    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
 28 26  1  0
 29 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3321810

   ---

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: 2.60

#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: 13.59

CX Basic pKa: 1.01

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.81

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