N-(((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)methyl)-2-(4-fluorophenyl)acetamide

ID: ALA4092968

PubChem CID: 137654214

Max Phase: Preclinical

Molecular Formula: C14H19FN2O4

Molecular Weight: 298.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(F)cc1)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H19FN2O4/c15-9-3-1-8(2-4-9)5-12(19)16-6-10-13(20)14(21)11(7-18)17-10/h1-4,10-11,13-14,17-18,20-21H,5-7H2,(H,16,19)/t10-,11+,13+,14-/m0/s1

Standard InChI Key:  IXEUZFAEYSCCLB-UNJBNNCHSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.4421   -4.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2593   -4.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136   -3.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1919   -3.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -3.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444   -2.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -4.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388   -4.9994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2912   -3.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4622   -2.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2397   -2.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108   -1.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8463   -2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6238   -2.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2284   -3.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0053   -2.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1769   -2.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5655   -1.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7909   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9541   -1.8027    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  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092968

   ---

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: 298.31

Molecular Weight (Monoisotopic): 298.1329

AlogP: -1.46

#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: 13.20

CX Basic pKa: 8.67

CX LogP: -1.20

CX LogD: -2.48

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: 0.05

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