(2R,3R,4S)-2-[((S)-2-Hydroxy-1-phenyl-ethylamino)-methyl]-pyrrolidine-3,4-diol

ID: ALA189366

PubChem CID: 11414083

Max Phase: Preclinical

Molecular Formula: C13H20N2O3

Molecular Weight: 252.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H20N2O3/c16-8-11(9-4-2-1-3-5-9)14-6-10-13(18)12(17)7-15-10/h1-5,10-18H,6-8H2/t10-,11-,12+,13-/m1/s1

Standard InChI Key:  OGMKEJTXCCFISS-FVCCEPFGSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    0.8051    0.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -0.1212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -0.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7101   -2.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5170   -2.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9295   -1.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500   -1.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775   -1.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -0.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    2.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906    2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196   -0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196   -0.9462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
 16  1  1  0
  1 17  1  0
  3  2  1  0
  4  3  1  1
  4  5  1  0
  9  4  1  0
  6  5  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  6
 12 11  2  0
 16 11  1  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA189366

   (2R,3R,4S)-2-({[(1S)-2-Hydroxy-1-phenylethyl]amino}methyl)pyrrolidine-3,4-diol

Molecule Features

Natural Product: Yes

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: 252.31

Molecular Weight (Monoisotopic): 252.1474

AlogP: -1.00

#Rotatable Bonds: 5

Polar Surface Area: 84.75

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.34

CX Basic pKa: 9.13

CX LogP: -0.84

CX LogD: -2.57

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.46

Np Likeness Score: 0.90

References

1. Fiaux H, Popowycz F, Favre S, Schütz C, Vogel P, Gerber-Lemaire S, Juillerat-Jeanneret L..  (2005)  Functionalized pyrrolidines inhibit alpha-mannosidase activity and growth of human glioblastoma and melanoma cells.,  48  (13): [PMID:15974577] [10.1021/jm0409019]

2. 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