{5-[3-(5-Carboxymethyl-thiophen-2-yl)-benzo[g]quinoxalin-2-yl]-thiophen-2-yl}-acetic acid

ID: ALA193162

PubChem CID: 10183039

Max Phase: Preclinical

Molecular Formula: C24H16N2O4S2

Molecular Weight: 460.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccc(-c2nc3cc4ccccc4cc3nc2-c2ccc(CC(=O)O)s2)s1

Standard InChI:  InChI=1S/C24H16N2O4S2/c27-21(28)11-15-5-7-19(31-15)23-24(20-8-6-16(32-20)12-22(29)30)26-18-10-14-4-2-1-3-13(14)9-17(18)25-23/h1-10H,11-12H2,(H,27,28)(H,29,30)

Standard InChI Key:  JKZIETFCILCHEP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    2.3417   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -2.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -0.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -0.9792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -3.1292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042    0.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6000   -3.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667    0.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5  2  1  0
  6  1  1  0
  7  5  1  0
  8  6  1  0
  9 10  1  0
 10  3  1  0
 11  7  1  0
 12  8  1  0
 13  5  2  0
 14  6  2  0
 15 11  1  0
 16 12  1  0
 17 14  1  0
 18 13  1  0
 19 10  2  0
 20  9  2  0
 21 15  1  0
 22 16  1  0
 23 24  1  0
 24 19  1  0
 25 21  2  0
 26 22  2  0
 27 22  1  0
 28 21  1  0
 29 24  2  0
 30 23  2  0
 31 32  2  0
 32 29  1  0
 12 17  2  0
  4  9  1  0
 11 18  2  0
 23 20  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA193162

   {5-[3-(5-Carboxymethyl-thiophen-2-yl)-benzo[g]quinoxalin-2-yl]-thiophen-2-yl}-acetic acid

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: 460.54

Molecular Weight (Monoisotopic): 460.0551

AlogP: 5.49

#Rotatable Bonds: 6

Polar Surface Area: 100.38

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.31

CX Basic pKa: ┄

CX LogP: 5.45

CX LogD: 0.04

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -0.48

References

1. Székelyhidi Z, Pató J, Wáczek F, Bánhegyi P, Hegymegi-Barakonyi B, Erös D, Mészáros G, Hollósy F, Hafenbradl D, Obert S, Klebl B, Kéri G, Orfi L..  (2005)  Synthesis of selective SRPK-1 inhibitors: novel tricyclic quinoxaline derivatives.,  15  (13): [PMID:15925511] [10.1016/j.bmcl.2005.04.064]

Source

Source(1):

• Scientific Literature