6-acetylamino-4-hydroxy-3-(4-sulfamoyl-phenylazo)-naphthalene-2,7-disulfonic acid

ID: ALA237251

Cas Number: 132-38-7

PubChem CID: 8625

Max Phase: Preclinical

Molecular Formula: C18H16N4O10S3

Molecular Weight: 544.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc2c(O)c(/N=N/c3ccc(S(N)(=O)=O)cc3)c(S(=O)(=O)O)cc2cc1S(=O)(=O)O

Standard InChI:  InChI=1S/C18H16N4O10S3/c1-9(23)20-14-8-13-10(6-15(14)34(27,28)29)7-16(35(30,31)32)17(18(13)24)22-21-11-2-4-12(5-3-11)33(19,25)26/h2-8,24H,1H3,(H,20,23)(H2,19,25,26)(H,27,28,29)(H,30,31,32)/b22-21+

Standard InChI Key:  RALNLQYPLYWQRT-QURGRASLSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    1.7625  -16.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542  -16.0917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9413  -16.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125  -11.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125  -11.5792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6001  -10.7780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181  -14.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2193  -15.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044  -16.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062  -14.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909  -14.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901  -15.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748  -16.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402  -15.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355  -14.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804  -14.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327  -14.4543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212  -13.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006  -13.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293  -13.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341  -16.1059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250  -16.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542  -16.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981  -15.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0848  -13.6239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474  -14.4392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708  -14.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5818  -13.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066  -13.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8175  -13.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035  -12.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742  -12.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1670  -13.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6385  -11.5781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692  -15.6805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 11 10  2  0
 18 19  1  0
 10  7  1  0
 18 20  2  0
  3  2  2  0
  8 21  1  0
  5  4  2  0
 21 22  2  0
 11 12  1  0
 21 23  2  0
  6  5  2  0
 21 24  1  0
 12 13  1  0
 16 25  1  0
  7  8  2  0
 15 26  1  0
 13 14  2  0
 26 27  2  0
 27 28  1  0
 14 15  1  0
 28 29  2  0
  8  9  1  0
 29 30  1  0
 15 16  2  0
 30 31  2  0
 16 11  1  0
 31 32  1  0
  9 12  2  0
 32 33  2  0
 33 28  1  0
 31  5  1  0
  7 17  1  0
  5 34  1  0
 14  2  1  0
  2  1  2  0
  2 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA237251

   PRONTOCIL

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: 544.55

Molecular Weight (Monoisotopic): 544.0029

AlogP: 2.06

#Rotatable Bonds: 6

Polar Surface Area: 242.95

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -3.10

CX Basic pKa: ┄

CX LogP: -2.40

CX LogD: -2.83

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.22

Np Likeness Score: -0.69

References

1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.,  15  (23): [PMID:17826101] [10.1016/j.bmc.2007.08.037]

2. Maresca A, Carta F, Vullo D, Scozzafava A, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Inhibition of the Rv1284 and Rv3273 beta-carbonic anhydrases from Mycobacterium tuberculosis with diazenylbenzenesulfonamides.,  19  (17): [PMID:19651511] [10.1016/j.bmcl.2009.07.088]

Source

Source(1):

• Scientific Literature