3-(1-(7-biphenyl-2-ylcarboxamidoheptyl)-1H-1,2,3-triazol-4-yl)pyridine 1-oxide

ID: ALA4070645

PubChem CID: 137638924

Max Phase: Preclinical

Molecular Formula: C27H29N5O2

Molecular Weight: 455.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCCCCn1cc(-c2ccc[n+]([O-])c2)nn1)c1ccccc1-c1ccccc1

Standard InChI:  InChI=1S/C27H29N5O2/c33-27(25-16-8-7-15-24(25)22-12-5-4-6-13-22)28-17-9-2-1-3-10-18-31-21-26(29-30-31)23-14-11-19-32(34)20-23/h4-8,11-16,19-21H,1-3,9-10,17-18H2,(H,28,33)

Standard InChI Key:  AEVRLOLYYRZQKE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   13.1097   -9.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2511   -9.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2505   -7.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4982   -9.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7906   -9.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9477   -9.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9681   -9.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1089   -8.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2505   -9.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9681   -6.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9681   -8.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1688   -8.5317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6818   -8.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9689   -9.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8246   -8.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5368   -6.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9681   -6.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6818   -7.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6825   -9.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1089   -7.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3954   -6.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2505   -8.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5368   -6.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9707   -9.9993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3961   -9.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8234   -9.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1276   -9.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3622   -8.3595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876   -9.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3954   -8.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2505   -5.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6447   -8.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5368   -9.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6347  -10.7483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
 14  2  1  0
 18 17  1  0
 19 14  1  0
 33 26  1  0
 18 21  1  0
 24  5  2  0
  3 23  1  0
 32 15  1  0
 23 16  2  0
 13 30  1  0
 12 28  2  0
  8 30  2  0
 17 10  1  0
 11  7  1  0
 22 11  2  0
 26  1  1  0
 20  8  1  0
 16 31  1  0
 21 20  2  0
 25 19  1  0
 15 29  2  0
 27  5  1  0
  6  4  2  0
 27 32  2  0
 31 10  2  0
  9 33  1  0
  2  4  1  0
  6 27  1  0
  2 12  1  0
 17  3  2  0
 13 18  2  0
 29 24  1  0
 28  6  1  0
 11 13  1  0
  1 25  1  0
 24 34  1  0
M  CHG  2  24   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4070645

   ---

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: 455.56

Molecular Weight (Monoisotopic): 455.2321

AlogP: 4.63

#Rotatable Bonds: 11

Polar Surface Area: 86.75

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.63

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.20

Np Likeness Score: -1.24

References

1. Travelli C, Aprile S, Rahimian R, Grolla AA, Rogati F, Bertolotti M, Malagnino F, di Paola R, Impellizzeri D, Fusco R, Mercalli V, Massarotti A, Stortini G, Terrazzino S, Del Grosso E, Fakhfouri G, Troiani MP, Alisi MA, Grosa G, Sorba G, Canonico PL, Orsomando G, Cuzzocrea S, Genazzani AA, Galli U, Tron GC..  (2017)  Identification of Novel Triazole-Based Nicotinamide Phosphoribosyltransferase (NAMPT) Inhibitors Endowed with Antiproliferative and Antiinflammatory Activity.,  60  (5): [PMID:28165742] [10.1021/acs.jmedchem.6b01392]

2. Travelli C, Aprile S, Mattoteia D, Colombo G, Clemente N, Scanziani E, Terrazzino S, Alisi MA, Polenzani L, Grosa G, Genazzani AA, Tron GC, Galli U..  (2019)  Identification of potent triazolylpyridine nicotinamide phosphoribosyltransferase (NAMPT) inhibitors bearing a 1,2,3-triazole tail group.,  181  [PMID:31400709] [10.1016/j.ejmech.2019.111576]

Source

Source(1):

• Scientific Literature