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

ID: ALA2206817

PubChem CID: 11277122

Max Phase: Preclinical

Molecular Formula: C14H22N2O3

Molecular Weight: 266.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@H](NC[C@H]1NC[C@H](O)[C@@H]1O)c1ccccc1

Standard InChI:  InChI=1S/C14H22N2O3/c1-19-9-12(10-5-3-2-4-6-10)15-7-11-14(18)13(17)8-16-11/h2-6,11-18H,7-9H2,1H3/t11-,12+,13+,14-/m1/s1

Standard InChI Key:  LBDZNBLTXQQPGI-ZOBORPQBSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   18.4635  -21.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6464  -21.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4022  -22.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0714  -22.9514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7238  -22.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9360  -21.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1582  -21.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5044  -22.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1042  -22.1477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8847  -22.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4845  -21.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2651  -22.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0655  -23.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4658  -23.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6461  -24.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4273  -24.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0284  -24.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8451  -23.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8649  -21.5216    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
  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
 12 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206817

   (2R,3R,4S)-2-[[[(1R)-2-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: 266.34

Molecular Weight (Monoisotopic): 266.1630

AlogP: -0.34

#Rotatable Bonds: 6

Polar Surface Area: 73.75

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: 9.13

CX LogP: -0.19

CX LogD: -1.92

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.57

Np Likeness Score: 0.78

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