(2S,4R)-4-hydroxy-N-[[4-(4-methylthiazol-5-yl)phenyl]methyl]-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

ID: ALA5170870

PubChem CID: 167719023

Max Phase: Preclinical

Molecular Formula: C18H18F3N3O3S

Molecular Weight: 413.42

Names and Identifiers

Canonical SMILES:  Cc1ncsc1-c1ccc(CNC(=O)[C@@H]2C[C@@H](O)CN2C(=O)C(F)(F)F)cc1

Standard InChI:  InChI=1S/C18H18F3N3O3S/c1-10-15(28-9-23-10)12-4-2-11(3-5-12)7-22-16(26)14-6-13(25)8-24(14)17(27)18(19,20)21/h2-5,9,13-14,25H,6-8H2,1H3,(H,22,26)/t13-,14+/m1/s1

Standard InChI Key:  YZPLZOZNVWZFST-KGLIPLIRSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -1.6089   -0.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9651   -1.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822   -0.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5079   -0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2445   -0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -0.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176    0.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542    0.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1879    0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3137   -0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    1.0477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4019    1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865    1.6585    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275    0.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2909    0.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    0.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449    0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    1.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    0.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -0.4026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5970   -1.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0158   -1.7843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9757   -0.8233    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6113   -2.2050    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1924   -1.6194    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
 10  9  1  0
 11 10  2  0
 11 12  1  0
 13 11  1  0
 14 13  2  0
 15 14  1  0
 10 15  1  0
  9 16  2  0
 16 17  1  0
 17  6  2  0
 18  1  1  0
 19 18  1  0
 19 20  1  6
 21 19  1  0
 22 21  1  0
  1 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 24 28  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5170870

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 413.42

Molecular Weight (Monoisotopic): 413.1021

AlogP: 2.26

#Rotatable Bonds: 4

Polar Surface Area: 82.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.62

CX Basic pKa: 2.65

CX LogP: 1.07

CX LogD: 1.07

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.81

Np Likeness Score: -1.11

References

1. de Castro GV, Ciulli A..  (2021)  Estimating the cooperativity of PROTAC-induced ternary complexes using ¹⁹F NMR displacement assay.,  12  (10.0): [PMID:34778777] [10.1039/D1MD00215E]

Source

Source(1):

• Scientific Literature