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

ID: ALA188227

PubChem CID: 11290388

Max Phase: Preclinical

Molecular Formula: C19H24N2O3

Molecular Weight: 328.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H24N2O3/c22-16-12-20-15(19(16)24)11-21-17(13-7-3-1-4-8-13)18(23)14-9-5-2-6-10-14/h1-10,15-24H,11-12H2/t15-,16+,17-,18+,19-/m1/s1

Standard InChI Key:  MAKKYIXPCPJUFC-MTHXSQLBSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
   -3.2833   -7.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -6.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625   -6.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5583   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500   -7.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -7.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958   -5.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -6.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9708   -5.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -7.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -8.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -5.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -9.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875   -8.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -9.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3  2  1  1
  4  5  1  0
  5  1  1  0
  6  3  1  0
  7  8  1  0
  8  1  1  0
  5  9  1  1
 10  3  1  0
  6 11  1  6
  4 12  1  6
 13  6  1  0
  7 14  1  6
 15 10  1  0
 16 10  2  0
 17 11  2  0
 18 11  1  0
 19 16  1  0
 20 17  1  0
 21 18  2  0
 22 15  2  0
 23 19  2  0
 24 21  1  0
  4  7  1  0
 22 23  1  0
 20 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA188227

   (2R,3R,4S)-2-[[[(1R,2S)-2-hydroxy-1,2-diphenylethyl]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: 328.41

Molecular Weight (Monoisotopic): 328.1787

AlogP: 0.74

#Rotatable Bonds: 6

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: 13.21

CX Basic pKa: 9.14

CX LogP: 0.95

CX LogD: -0.79

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: 0.70

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