2-hydroxy-5-[(2-oxo-1H-benzo[cd]indol-6-yl)sulfonylamino]benzoic acid

ID: ALA4538480

PubChem CID: 6483726

Max Phase: Preclinical

Molecular Formula: C18H12N2O6S

Molecular Weight: 384.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(NS(=O)(=O)c2ccc3c4c(cccc24)C(=O)N3)ccc1O

Standard InChI:  InChI=1S/C18H12N2O6S/c21-14-6-4-9(8-12(14)18(23)24)20-27(25,26)15-7-5-13-16-10(15)2-1-3-11(16)17(22)19-13/h1-8,20-21H,(H,19,22)(H,23,24)

Standard InChI Key:  ALNRIGYRTBFZIT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.7080  -13.8221    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8904  -13.8175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851  -11.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5840  -12.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920  -13.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9996  -12.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7082  -13.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4164  -12.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117  -11.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7005  -11.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720  -10.5789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5781  -10.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2914  -11.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093   -9.9051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4184  -14.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1251  -13.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8311  -14.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5374  -13.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5358  -13.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8222  -12.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188  -13.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2420  -12.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2458  -14.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2474  -15.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9528  -13.8176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  9 10  1  0
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 15 11  1  0
 14 16  2  0
  8  2  1  0
  2 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
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 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 20 25  1  0
 25 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538480

   2-Hydroxy-5-{[(2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)sulfonyl]amino}benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 384.37

Molecular Weight (Monoisotopic): 384.0416

AlogP: 2.61

#Rotatable Bonds: 4

Polar Surface Area: 132.80

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.66

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: -1.05

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -0.99

References

1. Wang Y, Dou X, Jiang L, Jin H, Zhang L, Zhang L, Liu Z..  (2019)  Discovery of novel glycogen synthase kinase-3α inhibitors: Structure-based virtual screening, preliminary SAR and biological evaluation for treatment of acute myeloid leukemia.,  171  [PMID:30925338] [10.1016/j.ejmech.2019.03.039]

Source

Source(1):

• Scientific Literature