6,7-Di-thiophen-2-yl-2,3-dihydro-1,4-dioxa-5,8-diaza-anthracene-2-carboxylic acid

ID: ALA193232

PubChem CID: 44399002

Max Phase: Preclinical

Molecular Formula: C19H12N2O4S2

Molecular Weight: 396.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1COc2cc3nc(-c4cccs4)c(-c4cccs4)nc3cc2O1

Standard InChI:  InChI=1S/C19H12N2O4S2/c22-19(23)14-9-24-12-7-10-11(8-13(12)25-14)21-18(16-4-2-6-27-16)17(20-10)15-3-1-5-26-15/h1-8,14H,9H2,(H,22,23)

Standard InChI Key:  GPBNOEVRRDJTGH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.9792   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -1.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625    0.3458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042    0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -1.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -0.0167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -2.1250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    1.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292    1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -0.0667    0.0000 O   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  7  1  0
  6 19  1  0
  7 12  2  0
  8  9  1  0
  9  3  1  0
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 11  2  1  0
 12 14  1  0
 13  8  2  0
 14  9  2  0
 15  6  1  0
 16 12  1  0
 17 11  1  0
 18 10  1  0
 19 16  1  0
 20 10  2  0
 21 11  2  0
 22 17  1  0
 23 18  1  0
 24 15  2  0
 25 20  1  0
 26 21  1  0
 27 15  1  0
 23 25  2  0
  4  8  1  0
  7 13  1  0
 22 26  2  0
  5  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA193232

   6,7-Di-thiophen-2-yl-2,3-dihydro-1,4-dioxa-5,8-diaza-anthracene-2-carboxylic 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: 396.45

Molecular Weight (Monoisotopic): 396.0238

AlogP: 4.31

#Rotatable Bonds: 3

Polar Surface Area: 81.54

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: 0.55

CX LogP: 4.12

CX LogD: 0.94

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: -0.54

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