(2R,3R,4S)-2-(((R)-2-((2-fluorophenoxy)methoxy)-1-phenylethylamino)methyl)pyrrolidine-3,4-diol

ID: ALA2206820

PubChem CID: 71455988

Max Phase: Preclinical

Molecular Formula: C20H25FN2O4

Molecular Weight: 376.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@H]1[C@@H](O)CN[C@@H]1CN[C@@H](COCOc1ccccc1F)c1ccccc1

Standard InChI:  InChI=1S/C20H25FN2O4/c21-15-8-4-5-9-19(15)27-13-26-12-17(14-6-2-1-3-7-14)22-10-16-20(25)18(24)11-23-16/h1-9,16-18,20,22-25H,10-13H2/t16-,17+,18+,20-/m1/s1

Standard InChI Key:  FYORRKSEMNGZQH-DOADOZAASA-N

Molfile:  

     RDKit          2D

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   10.5599  -28.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3158  -29.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9850  -30.2030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6374  -29.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8495  -28.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0717  -28.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4179  -29.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0177  -29.3992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7983  -29.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3981  -29.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1786  -29.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9790  -30.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3794  -30.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5596  -31.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3409  -32.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9420  -31.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7587  -30.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7785  -28.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5977  -27.9762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172  -27.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6401  -26.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8603  -26.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2596  -27.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4438  -28.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2233  -28.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2411  -26.3851    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
  1  6  1  6
  2  7  1  6
  5  8  1  1
  8  9  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
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 17 18  2  0
 18 13  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206820

   (2R,3R,4S)-2-[[[(1R)-2-[(2-fluorophenoxy)methoxy]-1-phenylethyl]amino]methyl]pyrrolidine-3,4-diol

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: 376.43

Molecular Weight (Monoisotopic): 376.1798

AlogP: 1.20

#Rotatable Bonds: 9

Polar Surface Area: 82.98

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: 9.13

CX LogP: 1.70

CX LogD: -0.03

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: 0.08

References

1. Moorthy NS, Brás NF, Ramos MJ, Fernandes PA..  (2012)  Virtual screening and QSAR study of some pyrrolidine derivatives as α-mannosidase inhibitors for binding feature analysis.,  20  (24): [PMID:23151473] [10.1016/j.bmc.2012.10.011]

Source

Source(1):

• Scientific Literature