(2S,4R)-N-(4-bromobenzyl)-4-hydroxy-1-(3,3,3-trifluoropropanoyl)pyrrolidine-2-carboxamide

ID: ALA5177407

PubChem CID: 168276187

Max Phase: Preclinical

Molecular Formula: C15H16BrF3N2O3

Molecular Weight: 409.20

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(Br)cc1)[C@@H]1C[C@@H](O)CN1C(=O)CC(F)(F)F

Standard InChI:  InChI=1S/C15H16BrF3N2O3/c16-10-3-1-9(2-4-10)7-20-14(24)12-5-11(22)8-21(12)13(23)6-15(17,18)19/h1-4,11-12,22H,5-8H2,(H,20,24)/t11-,12+/m1/s1

Standard InChI Key:  HZXVIHSWGKQYTM-NEPJUHHUSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -0.5328    0.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002    1.1431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453    1.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203    1.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    1.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9848    0.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1563    0.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5979    1.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    2.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394    2.7992    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418    2.5021    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548    3.0541    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -0.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3250   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3250   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6105   -3.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8960   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0394   -3.0541    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  1  6
  2  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  1 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 20 23  1  0
 14 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5177407

   ---

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: 409.20

Molecular Weight (Monoisotopic): 408.0296

AlogP: 1.98

#Rotatable Bonds: 4

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.79

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -1.10

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