SID48410298

ID: ALA1735214

PubChem CID: 24178231

Max Phase: Preclinical

Molecular Formula: C23H16N4O3

Molecular Weight: 396.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1)Nc1ccc2nc(-c3ccco3)c(-c3ccco3)nc2c1

Standard InChI:  InChI=1S/C23H16N4O3/c28-23(24-15-6-2-1-3-7-15)25-16-10-11-17-18(14-16)27-22(20-9-5-13-30-20)21(26-17)19-8-4-12-29-19/h1-14H,(H2,24,25,28)

Standard InChI Key:  NZLWNHRZGRQNIW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   -2.1683    0.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008    2.6628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578   -1.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0143    0.1923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0143    1.8423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722    0.1923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5867   -1.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    0.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    1.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288    0.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288    1.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146    1.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578    0.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    1.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578    1.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008   -0.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683    1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203   -0.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078   -0.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    2.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    2.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722   -0.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5867   -1.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722   -2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -3.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722   -3.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5867   -3.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0
  1 20  1  0
  2 13  1  0
  2 22  1  0
  3 24  2  0
  4  8  2  0
  4 10  1  0
  5  9  2  0
  5 11  1  0
  6 15  1  0
  6 24  1  0
  7 24  1  0
  7 25  1  0
  8  9  1  0
  8 12  1  0
  9 13  1  0
 10 11  2  0
 10 14  1  0
 11 16  1  0
 12 18  2  0
 13 19  2  0
 14 15  2  0
 15 17  1  0
 16 17  2  0
 18 21  1  0
 19 23  1  0
 20 21  2  0
 22 23  2  0
 25 26  2  0
 25 27  1  0
 26 28  1  0
 27 29  2  0
 28 30  2  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1735214

   1-[2,3-Bis(2-furanyl)-6-quinoxalinyl]-3-phenylurea

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: 396.41

Molecular Weight (Monoisotopic): 396.1222

AlogP: 5.79

#Rotatable Bonds: 4

Polar Surface Area: 93.19

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.41

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -1.30

References

1. PubChem BioAssay data set, 

2. Chen Q, Bryant VC, Lopez H, Kelly DL, Luo X, Natarajan A..  (2011)  2,3-Substituted quinoxalin-6-amine analogs as antiproliferatives: a structure-activity relationship study.,  21  (7): [PMID:21376584] [10.1016/j.bmcl.2011.02.055]

3. Rajule R, Bryant VC, Lopez H, Luo X, Natarajan A..  (2012)  Perturbing pro-survival proteins using quinoxaline derivatives: a structure-activity relationship study.,  20  (7): [PMID:22386982] [10.1016/j.bmc.2012.02.022]

4. Sagar S, Singh S, Mallareddy JR, Sonawane YA, Napoleon JV, Rana S, Contreras JI, Rajesh C, Ezell EL, Kizhake S, Garrison JC, Radhakrishnan P, Natarajan A..  (2021)  Structure activity relationship (SAR) study identifies a quinoxaline urea analog that modulates IKKβ phosphorylation for pancreatic cancer therapy.,  222  [PMID:34098465] [10.1016/j.ejmech.2021.113579]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays