4-(2-hydroxy-3-methoxybenzylamino)-N-(pyridin-3-yl)benzenesulfonamide

ID: ALA3113189

PubChem CID: 70701398

Max Phase: Preclinical

Molecular Formula: C19H19N3O4S

Molecular Weight: 385.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2ccc(S(=O)(=O)Nc3cccnc3)cc2)c1O

Standard InChI:  InChI=1S/C19H19N3O4S/c1-26-18-6-2-4-14(19(18)23)12-21-15-7-9-17(10-8-15)27(24,25)22-16-5-3-11-20-13-16/h2-11,13,21-23H,12H2,1H3

Standard InChI Key:  PGTOEVVTANJYML-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.5150  -11.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094  -10.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027  -11.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240  -10.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2538  -10.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4966   -5.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -9.8690    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7905   -7.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9632   -9.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7851   -9.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4437   -6.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2040   -7.0293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4490   -4.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6749   -5.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1987   -8.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259   -7.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441  -10.6869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -8.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2654   -6.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9144   -4.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6695   -7.0386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2708   -4.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0312   -5.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686   -7.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317   -9.8701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372  -11.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339  -11.9881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0
  3  1  2  0
 26  4  1  0
  2  3  1  0
  1 27  1  0
  9  7  1  0
  9 18  2  0
 11 19  1  0
 17  7  2  0
 22 13  2  0
 19 14  2  0
 10 15  2  0
 14  6  1  0
 16 11  1  0
  8 12  1  0
  8 24  2  0
 12 16  1  0
 15  8  1  0
  9 10  1  0
  7  5  2  0
  6 20  1  0
 13 23  1  0
 24 18  1  0
 14 22  1  0
 19 21  1  0
 11 23  2  0
  7 25  1  0
 25  4  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113189

   4-[(2-hydroxy-3-methoxyphenyl)methylamino]-N-pyridin-3-ylbenzenesulfonamide

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: 385.45

Molecular Weight (Monoisotopic): 385.1096

AlogP: 3.21

#Rotatable Bonds: 7

Polar Surface Area: 100.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: 3.31

CX LogP: 1.98

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.34

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