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

ID: ALA425723

PubChem CID: 11425273

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-MROQNXINSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -1.3961    0.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105    1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    0.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    0.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    0.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816   -0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816   -1.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961   -1.6390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    0.0110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7473   -0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618    0.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    0.8315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550    1.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7675    0.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5880    0.2023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2155   -0.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870   -1.1315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  6  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  6  7  1  0
  7  8  1  0
  7 10  1  1
  8  9  1  0
 11 10  1  0
 12 11  1  1
 12 13  1  0
 17 12  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA425723

   (2R,3R,4S)-2-({[(1R)-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. Fiaux H, Kuntz DA, Hoffman D, Janzer RC, Gerber-Lemaire S, Rose DR, Juillerat-Jeanneret L..  (2008)  Functionalized pyrrolidine inhibitors of human type II alpha-mannosidases as anti-cancer agents: optimizing the fit to the active site.,  16  (15): [PMID:18599296] [10.1016/j.bmc.2008.06.021]

3. 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