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

ID: ALA4101655

PubChem CID: 137660577

Max Phase: Preclinical

Molecular Formula: C15H22N2O5

Molecular Weight: 310.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1CC(=O)NC[C@@H]1N[C@H](CO)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H22N2O5/c1-22-12-5-3-2-4-9(12)6-13(19)16-7-10-14(20)15(21)11(8-18)17-10/h2-5,10-11,14-15,17-18,20-21H,6-8H2,1H3,(H,16,19)/t10-,11+,14+,15-/m0/s1

Standard InChI Key:  LLGLLFDXJKHINB-DRABBMOASA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   12.7737  -17.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5909  -17.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8453  -16.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1823  -16.3232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5236  -16.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7463  -16.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5760  -15.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2925  -18.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0705  -18.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6228  -16.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7939  -15.7548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5714  -15.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7424  -14.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1779  -16.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0069  -16.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2296  -17.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0584  -17.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6653  -18.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4461  -18.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6136  -17.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3898  -17.1354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9992  -17.6800    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  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
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101655

   ---

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: 310.35

Molecular Weight (Monoisotopic): 310.1529

AlogP: -1.59

#Rotatable Bonds: 6

Polar Surface Area: 111.05

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 8.67

CX LogP: -1.50

CX LogD: -2.78

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.43

Np Likeness Score: 0.35

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