N-(5-(aminomethyl)-4-(3-nitrophenyl)thiazol-2-yl)-3,4-dimethoxybenzenesulfonamide

ID: ALA3526743

PubChem CID: 118753129

Max Phase: Preclinical

Molecular Formula: C18H18N4O6S2

Molecular Weight: 450.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)Nc2nc(-c3cccc([N+](=O)[O-])c3)c(CN)s2)cc1OC

Standard InChI:  InChI=1S/C18H18N4O6S2/c1-27-14-7-6-13(9-15(14)28-2)30(25,26)21-18-20-17(16(10-19)29-18)11-4-3-5-12(8-11)22(23)24/h3-9H,10,19H2,1-2H3,(H,20,21)

Standard InChI Key:  IXIGNBSHCYBEDA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.1610   -6.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531   -6.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3706   -6.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968   -6.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997   -5.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5835   -5.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1852   -4.7632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682   -4.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6081   -4.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6130   -6.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0126   -6.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8147   -6.7925    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9088   -5.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1644   -5.6402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6204   -5.5779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6284   -4.7608    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3400   -4.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8725   -5.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644   -4.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0426   -4.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7538   -4.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7622   -3.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0535   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3452   -3.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4733   -3.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1776   -3.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0586   -2.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7688   -1.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997   -7.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7825   -7.6528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  7  9  1  0
  6  7  1  0
 11 12  1  0
 10 11  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
  4 10  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 16 19  2  0
 17 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 17  1  0
 22 25  1  0
 25 26  1  0
 23 27  1  0
 27 28  1  0
 11 29  1  0
 29 30  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3526743

   ---

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: 450.50

Molecular Weight (Monoisotopic): 450.0668

AlogP: 3.00

#Rotatable Bonds: 8

Polar Surface Area: 146.68

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.89

CX Basic pKa: 8.12

CX LogP: 1.86

CX LogD: 1.83

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: -1.77

References

1. Beconi MG, Yates D, Lyons K, Matthews K, Clifton S, Mead T, Prime M, Winkler D, O'Connell C, Walter D, Toledo-Sherman L, Munoz-Sanjuan I, Dominguez C..  (2012)  Metabolism and pharmacokinetics of JM6 in mice: JM6 is not a prodrug for Ro-61-8048.,  40  (12): [PMID:22942319] [10.1124/dmd.112.046532]

Source

Source(1):

• Scientific Literature