(2R,3R,4S)-2-(Benzylamino-methyl)-pyrrolidine-3,4-diol

ID: ALA363475

Cas Number: 388076-96-8

PubChem CID: 10331137

Max Phase: Preclinical

Molecular Formula: C12H18N2O2

Molecular Weight: 222.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@H]1[C@@H](O)CN[C@@H]1CNCc1ccccc1

Standard InChI:  InChI=1S/C12H18N2O2/c15-11-8-14-10(12(11)16)7-13-6-9-4-2-1-3-5-9/h1-5,10-16H,6-8H2/t10-,11+,12-/m1/s1

Standard InChI Key:  SXQQUIDMNYCBEU-GRYCIOLGSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  1  0  0  0  0  0999 V2000
   -2.8125    0.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    0.9958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333    2.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250    2.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5  1  1  0
  6  9  1  0
  2  7  1  6
  4  8  1  6
  3  9  1  1
 10 11  1  0
 11  6  1  0
 12 10  2  0
 13 10  1  0
 14 13  2  0
 15 12  1  0
 16 14  1  0
  2  4  1  0
 15 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA363475

   (2R,3R,4S)-2-[(benzylamino)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: 222.29

Molecular Weight (Monoisotopic): 222.1368

AlogP: -0.53

#Rotatable Bonds: 4

Polar Surface Area: 64.52

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.35

CX Basic pKa: 9.16

CX LogP: -0.21

CX LogD: -1.97

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.55

Np Likeness Score: 0.67

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