N,N'-(Naphthalene-1,4-diyl)bis(4-methoxybenzamide)

ID: ALA3632890

PubChem CID: 1367926

Max Phase: Preclinical

Molecular Formula: C20H20N2O6S2

Molecular Weight: 448.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)Nc2ccc(NS(=O)(=O)c3ccc(OC)cc3)cc2)cc1

Standard InChI:  InChI=1S/C20H20N2O6S2/c1-27-17-7-11-19(12-8-17)29(23,24)21-15-3-5-16(6-4-15)22-30(25,26)20-13-9-18(28-2)10-14-20/h3-14,21-22H,1-2H3

Standard InChI Key:  GTIPSFWDUFHOOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.3421    3.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020    2.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3421   -3.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -2.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0126   -7.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132   -8.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -7.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6076   -5.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3194   -9.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3607  -10.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6076    5.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6107    7.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    8.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126    7.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    9.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   10.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  2  0
  6  5  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 12 13  1  0
 13  5  1  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
  9 22  1  0
 22  2  1  0
  2 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3632890

   Cambridge id 5528073

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: 448.52

Molecular Weight (Monoisotopic): 448.0763

AlogP: 3.31

#Rotatable Bonds: 8

Polar Surface Area: 110.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.13

CX Basic pKa: ┄

CX LogP: 2.63

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -0.82

References

1. Jain AD, Potteti H, Richardson BG, Kingsley L, Luciano JP, Ryuzoji AF, Lee H, Krunic A, Mesecar AD, Reddy SP, Moore TW..  (2015)  Probing the structural requirements of non-electrophilic naphthalene-based Nrf2 activators.,  103  [PMID:26363505] [10.1016/j.ejmech.2015.08.049]

2. Richardson BG, Jain AD, Potteti HR, Lazzara PR, David BP, Tamatam CR, Choma E, Skowron K, Dye K, Siddiqui Z, Wang YT, Krunic A, Reddy SP, Moore TW..  (2018)  Replacement of a Naphthalene Scaffold in Kelch-like ECH-Associated Protein 1 (KEAP1)/Nuclear Factor (Erythroid-derived 2)-like 2 (NRF2) Inhibitors.,  61  (17): [PMID:30122040] [10.1021/acs.jmedchem.8b01133]

Source

Source(1):

• Scientific Literature