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

ID: ALA4089066

PubChem CID: 137644200

Max Phase: Preclinical

Molecular Formula: C17H24N2O6

Molecular Weight: 352.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(/C=C/C(=O)NC[C@@H]2N[C@H](CO)[C@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C17H24N2O6/c1-24-11-4-5-14(25-2)10(7-11)3-6-15(21)18-8-12-16(22)17(23)13(9-20)19-12/h3-7,12-13,16-17,19-20,22-23H,8-9H2,1-2H3,(H,18,21)/b6-3+/t12-,13+,16+,17-/m0/s1

Standard InChI Key:  BVHOPALLLYRDTR-DUARSHAWSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   28.4077   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2249   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4792   -5.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8163   -5.0476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1575   -5.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3802   -5.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2100   -4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9265   -6.9669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7044   -6.9681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2568   -5.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4278   -4.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2053   -4.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3764   -3.4286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8119   -4.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6409   -5.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2474   -6.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0724   -6.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6782   -7.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4567   -7.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6260   -6.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0189   -5.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1864   -5.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9629   -4.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5068   -8.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7291   -8.5175    0.0000 C   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
 21 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089066

   ---

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: 352.39

Molecular Weight (Monoisotopic): 352.1634

AlogP: -1.11

#Rotatable Bonds: 7

Polar Surface Area: 120.28

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.67

CX LogP: -1.13

CX LogD: -2.42

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.39

Np Likeness Score: 0.61

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