4-fluoro-N-((R)-2,2,2-trifluoro-1-(4-((1S,2S)-2-(pyridin-3-yl)cyclopropane-1-carboxamido)phenyl)ethyl)benzamide

ID: ALA4203945

PubChem CID: 145977793

Max Phase: Preclinical

Molecular Formula: C24H19F4N3O2

Molecular Weight: 457.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H](c1ccc(NC(=O)[C@H]2C[C@@H]2c2cccnc2)cc1)C(F)(F)F)c1ccc(F)cc1

Standard InChI:  InChI=1S/C24H19F4N3O2/c25-17-7-3-15(4-8-17)22(32)31-21(24(26,27)28)14-5-9-18(10-6-14)30-23(33)20-12-19(20)16-2-1-11-29-13-16/h1-11,13,19-21H,12H2,(H,30,33)(H,31,32)/t19-,20+,21-/m1/s1

Standard InChI Key:  OYFJUOHKLAJUET-QHAWAJNXSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   35.9839  -28.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9827  -29.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6949  -29.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4087  -29.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4059  -28.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6931  -28.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5398  -28.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2532  -28.6906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5368  -27.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9635  -28.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6687  -28.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3785  -28.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3759  -27.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6576  -27.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9548  -27.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0857  -27.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   38.8248  -29.5097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.1108  -27.4667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   44.5041  -27.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2149  -27.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4979  -26.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.0815  -26.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2172  -28.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9272  -28.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6327  -28.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6239  -27.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9134  -27.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7871  -25.8085    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   42.3717  -25.8157    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   43.0759  -25.4031    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   47.3441  -28.6392    0.0000 F   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
  5 18  1  0
 19  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 19 18  1  0
 19 20  1  0
 18 20  1  0
 19 21  1  1
 18 22  1  6
 17 23  1  0
 23 24  1  0
 23 25  2  0
 16 26  1  6
 24 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 24  1  0
 26 32  1  0
 26 33  1  0
 26 34  1  0
 29 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4203945

   ---

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: 457.43

Molecular Weight (Monoisotopic): 457.1413

AlogP: 5.00

#Rotatable Bonds: 6

Polar Surface Area: 71.09

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.85

CX Basic pKa: 4.90

CX LogP: 4.15

CX LogD: 4.15

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: -1.43

References

1. Palacios DS, Meredith E, Kawanami T, Adams C, Chen X, Darsigny V, Geno E, Palermo M, Baird D, Boynton G, Busby SA, George EL, Guy C, Hewett J, Tierney L, Thigale S, Weihofen W, Wang L, White N, Yin M, Argikar UA..  (2018)  Structure based design of nicotinamide phosphoribosyltransferase (NAMPT) inhibitors from a phenotypic screen.,  28  (3): [PMID:29275937] [10.1016/j.bmcl.2017.12.037]

Source

Source(1):

• Scientific Literature