N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)-3-(4-(trifluoromethyl)phenyl)acrylamide

ID: ALA4100807

PubChem CID: 137660069

Max Phase: Preclinical

Molecular Formula: C16H19F3N2O4

Molecular Weight: 360.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(C(F)(F)F)cc1)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H19F3N2O4/c17-16(18,19)10-4-1-9(2-5-10)3-6-13(23)20-7-11-14(24)15(25)12(8-22)21-11/h1-6,11-12,14-15,21-22,24-25H,7-8H2,(H,20,23)/b6-3+/t11-,12+,14+,15-/m0/s1

Standard InChI Key:  YQJCECMJDJDFLF-WCXQHLLSSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   12.8604  -16.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6776  -16.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9320  -15.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2690  -15.2212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6103  -15.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8330  -15.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6627  -14.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3792  -17.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1572  -17.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7095  -15.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8805  -14.6528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6581  -14.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8291  -13.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2646  -14.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0936  -15.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7001  -16.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5252  -17.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1309  -17.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9094  -17.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0787  -16.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4717  -16.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5167  -17.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3467  -18.7359    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.2939  -17.6841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.0926  -18.5106    0.0000 F   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
  5  6  1  1
  6  7  1  0
  1  8  1  1
  2  9  1  1
  3 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100807

   ---

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: 360.33

Molecular Weight (Monoisotopic): 360.1297

AlogP: -0.11

#Rotatable Bonds: 5

Polar Surface Area: 101.82

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.19

CX Basic pKa: 8.67

CX LogP: 0.06

CX LogD: -1.22

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: 0.34

References

1. Cheng WC, Wang JH, Yun WY, Li HY, Hu JM..  (2017)  Rapid preparation of (3R,4S,5R) polyhydroxylated pyrrolidine-based libraries to discover a pharmacological chaperone for treatment of Fabry disease.,  126  [PMID:27744182] [10.1016/j.ejmech.2016.10.004]

Source

Source(1):

• Scientific Literature