(2R,3S,4S)-2,5-Bis-hydroxymethyl-pyrrolidine-3,4-diol

ID: ALA469844

Max Phase: Preclinical

Molecular Formula: C6H13NO4

Molecular Weight: 163.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1N[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5-,6+/m1/s1

Standard InChI Key:  PFYHYHZGDNWFIF-KAZBKCHUSA-N

Molfile:  

     RDKit          2D

 11 11  0  0  1  0  0  0  0  0999 V2000
    2.6761   -1.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -1.9978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    1.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2409    0.2079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -0.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610   -0.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9061    0.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735    1.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6
  9  2  1  6
  3 10  1  0
  4 11  1  0
  5  6  1  0
  5  7  1  0
  6  8  1  0
  6 10  1  6
  7  9  1  0
  7 11  1  1
  8  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA469844

   ---

2. Alternative Forms:

   

   ALA469844

   (2R,3S,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol;hydrochloride

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: 163.17

Molecular Weight (Monoisotopic): 163.0845

AlogP: -2.97

#Rotatable Bonds: 2

Polar Surface Area: 92.95

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 8.88

CX LogP: -2.89

CX LogD: -4.38

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.30

Np Likeness Score: 1.93

References

1. Wrodnigg TM, Withers SG, Stütz AE..  (2001)  Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are powerful beta-glucosidase inhibitors.,  11  (8): [PMID:11327590] [10.1016/s0960-894x(01)00126-3]

2. Hermetter A, Scholze H, Stütz AE, Withers SG, Wrodnigg TM..  (2001)  Powerful probes for glycosidases: novel, fluorescently tagged glycosidase inhibitors.,  11  (10): [PMID:11392550] [10.1016/s0960-894x(01)00209-8]

3. Asano N, Yamauchi T, Kagamifuchi K, Shimizu N, Takahashi S, Takatsuka H, Ikeda K, Kizu H, Chuakul W, Kettawan A, Okamoto T..  (2005)  Iminosugar-producing Thai medicinal plants.,  68  (8): [PMID:16124768] [10.1021/np050157a]

4. Kato A, Yamashita Y, Nakagawa S, Koike Y, Adachi I, Hollinshead J, Nash RJ, Ikeda K, Asano N..  (2010)  2,5-Dideoxy-2,5-imino-d-altritol as a new class of pharmacological chaperone for Fabry disease.,  18  (11): [PMID:20457528] [10.1016/j.bmc.2010.04.048]

5. Cheng WC, Wang JH, Li HY, Lu SJ, Hu JM, Yun WY, Chiu CH, Yang WB, Chien YH, Hwu WL..  (2016)  Bioevaluation of sixteen ADMDP stereoisomers toward alpha-galactosidase A: Development of a new pharmacological chaperone for the treatment of Fabry disease and potential enhancement of enzyme replacement therapy efficiency.,  123  [PMID:27474919] [10.1016/j.ejmech.2016.07.025]

6. Cheng WC, Wang JH, Yun WY, Li HY, Hu JM..  (2017)  Rapid preparation of (3R,4S,5R) polyhydroxylated pyrrolidine-based libraries to discover a pharmacological chaperone for treatment of Fabry disease.,  126  [PMID:27744182] [10.1016/j.ejmech.2016.10.004]

Source

Source(1):

• Scientific Literature