4-(2-hydroxy-3-methoxybenzylamino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

ID: ALA3113174

PubChem CID: 70701414

Max Phase: Preclinical

Molecular Formula: C18H19N3O5S

Molecular Weight: 389.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2ccc(S(=O)(=O)Nc3cc(C)on3)cc2)c1O

Standard InChI:  InChI=1S/C18H19N3O5S/c1-12-10-17(20-26-12)21-27(23,24)15-8-6-14(7-9-15)19-11-13-4-3-5-16(25-2)18(13)22/h3-10,19,22H,11H2,1-2H3,(H,20,21)

Standard InChI Key:  MAHHNZSNKYONTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.1746  -17.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8396  -17.0902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5986  -16.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7803  -16.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5181  -17.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7409  -17.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7668  -14.9019    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0291  -14.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0942  -15.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1787  -14.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0001  -14.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4128  -13.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0001  -12.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1787  -12.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7701  -13.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0907  -15.6595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4128  -12.0612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2341  -12.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6468  -11.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4681  -11.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8767  -10.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4681   -9.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6468   -9.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2341  -10.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6980  -10.6389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1108   -9.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8767  -12.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  5  6  1  0
  8  7  2  0
  7  9  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
  7 16  1  0
 10  7  1  0
 16  3  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 25 26  1  0
 21 25  1  0
 20 27  1  0
 17 18  1  0
 13 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113174

   4-[(2-hydroxy-3-methoxyphenyl)methylamino]-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide

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: 389.43

Molecular Weight (Monoisotopic): 389.1045

AlogP: 3.11

#Rotatable Bonds: 7

Polar Surface Area: 113.69

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.15

CX Basic pKa: 1.94

CX LogP: 2.36

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -1.62

References

1. Luci DK, Jameson JB, Yasgar A, Diaz G, Joshi N, Kantz A, Markham K, Perry S, Kuhn N, Yeung J, Kerns EH, Schultz L, Holinstat M, Nadler JL, Taylor-Fishwick DA, Jadhav A, Simeonov A, Holman TR, Maloney DJ..  (2014)  Synthesis and structure-activity relationship studies of 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide derivatives as potent and selective inhibitors of 12-lipoxygenase.,  57  (2): [PMID:24393039] [10.1021/jm4016476]

Source

Source(1):

• Scientific Literature