ID: ALA110830

Max Phase: Preclinical

Molecular Formula: C5H11NO3

Molecular Weight: 133.15

Molecule Type: Small molecule

Representations

Synonyms (2): dideoxyiminoxylitol | Piperidine-3,4,5-Triol
Synonyms from Alternative Forms(2):

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

Standard InChI:  InChI=1S/C5H11NO3/c7-3-1-6-2-4(8)5(3)9/h3-9H,1-2H2/t3-,4+,5+

Standard InChI Key:  RMCNETIHECSPMZ-SCDXWVJYSA-N

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

Properties

Molecular Weight: 133.15

Molecular Weight (Monoisotopic): 133.0739

AlogP: -2.33

#Rotatable Bonds: 0

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.98

CX Basic pKa: 8.53

CX LogP: -2.26

CX LogD: -3.42

Aromatic Rings: 0

Heavy Atoms: 9

QED Weighted: 0.30

Np Likeness Score: 1.47

References

1. Berger A, Dax K, Gradnig G, Grassberger V, Stutz A, Ungerank M, Legler G, Bause E.  (1992)  Synthesis and biological activity of C-6 modified derivatives of the glucosidase inhibitor 1-deoxynojirimycin.,  2  (1): [10.1016/S0960-894X(00)80648-4]

2. Igarashi Y, Ichikawa M, Ichikawa Y.  (1996)  Synthesis of a new inhibitor of -fucosidase,  6  (5): [10.1016/0960-894X(96)00068-6]

3. Greimel P, Häusler H, Lundt I, Rupitz K, Stütz AE, Tarling CA, Withers SG, Wrodnigg TM..  (2006)  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.,  16  (8): [PMID:16481162] [10.1016/j.bmcl.2006.01.095]

4. Kuriyama C, Kamiyama O, Ikeda K, Sanae F, Kato A, Adachi I, Imahori T, Takahata H, Okamoto T, Asano N..  (2008)  In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.,  16  (15): [PMID:18595718] [10.1016/j.bmc.2008.06.026]

5. Goddard-Borger ED, Tropak MB, Yonekawa S, Tysoe C, Mahuran DJ, Withers SG..  (2012)  Rapid assembly of a library of lipophilic iminosugars via the thiol-ene reaction yields promising pharmacological chaperones for the treatment of Gaucher disease.,  55  (6): [PMID:22360565] [10.1021/jm201633y]

6. Zoidl M, Müller B, Torvisco A, Tysoe C, Benazza M, Siriwardena A, Withers SG, Wrodnigg TM..  (2014)  Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy.,  24  (12): [PMID:24803362] [10.1016/j.bmcl.2014.03.069]

7. Santos C, Stauffert F, Ballereau S, Dehoux C, Rodriguez F, Bodlenner A, Compain P, Génisson Y..  (2017)  Iminosugar-based ceramide mimicry for the design of new CERT START domain ligands.,  25  (6): [PMID:28237558] [10.1016/j.bmc.2017.02.026]

8. Wang JZ, Shimadate Y, Kise M, Kato A, Jia YM, Li YX, Fleet GWJ, Yu CY..  (2022)  trans, trans-2-C-Aryl-3,4-dihydroxypyrrolidines as potent and selective β-glucosidase inhibitors: Pharmacological chaperones for Gaucher disease.,  238  [PMID:35675756] [10.1016/j.ejmech.2022.114499]

Source

Source(1):

• Scientific Literature