Trifluoro-methanesulfonic acid 8-(3-nitro-phenyl)-[1,7]naphthyridin-6-yl ester

ID: ALA351900

PubChem CID: 10810934

Max Phase: Preclinical

Molecular Formula: C15H8F3N3O5S

Molecular Weight: 399.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(-c2nc(OS(=O)(=O)C(F)(F)F)cc3cccnc23)c1

Standard InChI:  InChI=1S/C15H8F3N3O5S/c16-15(17,18)27(24,25)26-12-8-10-4-2-6-19-13(10)14(20-12)9-3-1-5-11(7-9)21(22)23/h1-8H

Standard InChI Key:  ZHSRABCDAAITJX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    0.2167   -0.4875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -3.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -0.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -1.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958    0.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -2.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -3.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917    0.1000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -0.3917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    0.4375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 10  1  0
  4  1  1  0
  5  7  1  0
  6  4  1  0
  7  6  2  0
  8 11  1  0
  9  5  1  0
 10 12  2  0
 11 16  2  0
 12  9  1  0
 13  1  2  0
 14  1  2  0
 15  3  1  0
 16  6  1  0
 17  8  1  0
 18  3  2  0
 19  2  1  0
 20  2  1  0
 21  2  1  0
 22  9  2  0
 23 24  2  0
 24 22  1  0
 25 11  1  0
 26 27  1  0
 27 25  2  0
  8  5  2  0
 17 26  2  0
 23 10  1  0
M  CHG  2   3   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA351900

   6-Trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine

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: 399.31

Molecular Weight (Monoisotopic): 399.0137

AlogP: 3.43

#Rotatable Bonds: 4

Polar Surface Area: 112.29

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.83

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -1.22

References

1. Hersperger R, Bray-French K, Mazzoni L, Müller T..  (2000)  Palladium-catalyzed cross-coupling reactions for the synthesis of 6, 8-disubstituted 1,7-naphthyridines: a novel class of potent and selective phosphodiesterase type 4D inhibitors.,  43  (4): [PMID:10691693] [10.1021/jm991094u]

Source

Source(1):

• Scientific Literature