isobutyl N-(5-(5,6-difluoro-1H-indol-2-yl)-2-methoxyphenyl)sulfamoylcarbamate

ID: ALA5077863

PubChem CID: 9933617

Max Phase: Preclinical

Molecular Formula: C20H21F2N3O5S

Molecular Weight: 453.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc3cc(F)c(F)cc3[nH]2)cc1NS(=O)(=O)NC(=O)OCC(C)C

Standard InChI:  InChI=1S/C20H21F2N3O5S/c1-11(2)10-30-20(26)25-31(27,28)24-18-7-12(4-5-19(18)29-3)16-8-13-6-14(21)15(22)9-17(13)23-16/h4-9,11,23-24H,10H2,1-3H3,(H,25,26)

Standard InChI Key:  TZVQBYGXSQTCLW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.4984    2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838    2.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    1.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7820    0.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    1.0631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2872    2.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8022    1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770    1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642    2.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584    2.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712    1.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2619    1.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626    1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2131    2.5555    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2131    0.9017    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4963    1.7295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6746    0.3030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    0.3030    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9123   -0.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501   -1.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501    0.3030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753   -1.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3879   -1.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2131   -1.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753   -2.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157    0.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    1.1282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  2  0
  9  7  1  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 10 15  1  0
 15 14  2  0
  1 16  1  0
  6 17  1  0
 13 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 21 30  2  0
 21 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5077863

   2-methylpropyl N-[[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxyphenyl]sulfamoyl]carbamate

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: 453.47

Molecular Weight (Monoisotopic): 453.1170

AlogP: 4.16

#Rotatable Bonds: 7

Polar Surface Area: 109.52

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.74

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 2.59

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -1.07

References

1. Golovanov A, Zhuravlev A, Cruz A, Aksenov V, Shafiullina R, Kakularam KR, Lluch JM, Kuhn H, González-Lafont À, Ivanov I..  (2022)  N-Substituted 5-(1H-Indol-2-yl)-2-methoxyanilines Are Allosteric Inhibitors of the Linoleate Oxygenase Activity of Selected Mammalian ALOX15 Orthologs: Mechanism of Action.,  65  (3.0): [PMID:35073698] [10.1021/acs.jmedchem.1c01563]

Source

Source(1):

• Scientific Literature