N-(7-(4-(Pyridin-3-yl)-1H-1,2,3-triazol-1-yl)heptyl)-[1,1'-biphenyl]-2-carboxamide

ID: ALA4061448

PubChem CID: 86298751

Max Phase: Preclinical

Molecular Formula: C27H29N5O

Molecular Weight: 439.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCCCCCCn1cc(-c2cccnc2)nn1)c1ccccc1-c1ccccc1

Standard InChI:  InChI=1S/C27H29N5O/c33-27(25-16-8-7-15-24(25)22-12-5-4-6-13-22)29-18-9-2-1-3-10-19-32-21-26(30-31-32)23-14-11-17-28-20-23/h4-8,11-17,20-21H,1-3,9-10,18-19H2,(H,29,33)

Standard InChI Key:  WHPQEOJGGBKHCT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   47.7244   -8.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   48.4388   -9.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.1534   -8.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.1534   -7.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.4388   -7.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.7244   -7.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   47.0099   -6.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.7244   -6.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.4388   -6.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.8679   -7.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   50.5823   -8.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.8679   -9.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.4388  -10.0399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   47.7244  -10.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.0099  -10.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   45.5810  -10.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   44.1521  -10.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4375  -10.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7230  -10.0399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.6369   -9.2194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.8299   -9.0479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4173   -9.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5968   -9.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1119   -9.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2914   -9.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9559  -10.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4409  -10.6885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2613  -10.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9694  -10.3754    0.0000 C   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  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  5 10  1  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  3 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 27 32  1  0
 26 33  2  0
 23 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4061448

   2-phenyl-N-[7-(4-pyridin-3-yltriazol-1-yl)heptyl]benzamide

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: 439.56

Molecular Weight (Monoisotopic): 439.2372

AlogP: 5.39

#Rotatable Bonds: 11

Polar Surface Area: 72.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.08

CX LogP: 5.27

CX LogD: 5.27

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -1.38

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