(2R,3R,4S,5R)-2-(((R)-2-hydroxy-1-phenylethylamino)methyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol

ID: ALA2206816

PubChem CID: 11737619

Max Phase: Preclinical

Molecular Formula: C14H22N2O4

Molecular Weight: 282.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H](NC[C@H]1N[C@H](CO)[C@H](O)[C@@H]1O)c1ccccc1

Standard InChI:  InChI=1S/C14H22N2O4/c17-7-11(9-4-2-1-3-5-9)15-6-10-13(19)14(20)12(8-18)16-10/h1-5,10-20H,6-8H2/t10-,11+,12-,13-,14+/m1/s1

Standard InChI Key:  SEVCWNIQSBMQIX-ITGHMWBKSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   11.6288  -21.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8117  -21.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5675  -22.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2368  -22.9597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8891  -22.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1013  -21.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235  -21.0510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6697  -22.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2695  -22.1559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0500  -22.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6499  -21.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4304  -22.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2308  -23.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6311  -23.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8114  -24.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5926  -24.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1938  -24.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0104  -23.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7933  -22.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1797  -22.2083    0.0000 O   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
 16 17  1  0
 17 18  2  0
 18 13  1  0
  3 19  1  6
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206816

   (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[[[(1R)-2-hydroxy-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: 282.34

Molecular Weight (Monoisotopic): 282.1580

AlogP: -1.64

#Rotatable Bonds: 6

Polar Surface Area: 104.98

Molecular Species: BASE

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.20

CX Basic pKa: 8.68

CX LogP: -1.47

CX LogD: -2.77

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.37

Np Likeness Score: 0.87

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