1,4-dideoxy-1,4-imino-L-arabinitol

ID: ALA406973

Chembl Id: CHEMBL406973

Cas Number: 100937-53-9

PubChem CID: 127716

Max Phase: Preclinical

Molecular Formula: C5H11NO3

Molecular Weight: 133.15

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C5H11NO3/c7-2-3-5(9)4(8)1-6-3/h3-9H,1-2H2/t3-,4-,5-/m0/s1

Standard InChI Key:  OQEBIHBLFRADNM-YUPRTTJUSA-N

Alternative Forms

1. Parent:

   

   ALA406973

   1,4-Dideoxy-1,4-imino-L-arabinitol

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: 133.15

Molecular Weight (Monoisotopic): 133.0739

AlogP: -2.33

#Rotatable Bonds: 1

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: 13.32

CX Basic pKa: 9.36

CX LogP: -2.26

CX LogD: -4.20

Aromatic Rings: 0

Heavy Atoms: 9

QED Weighted: 0.32

Np Likeness Score: 2.76

References

1. Minami Y, Kuriyama C, Ikeda K, Kato A, Takebayashi K, Adachi I, Fleet GW, Kettawan A, Okamoto T, Asano N..  (2008)  Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.,  16  (6): [PMID:18258441] [10.1016/j.bmc.2008.01.032]

2. Kato A, Hayashi E, Miyauchi S, Adachi I, Imahori T, Natori Y, Yoshimura Y, Nash RJ, Shimaoka H, Nakagome I, Koseki J, Hirono S, Takahata H..  (2012)  α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.,  55  (23): [PMID:23106358] [10.1021/jm301304e]

3. Mena-Barragán T, García-Moreno MI, Nanba E, Higaki K, Concia AL, Clapés P, García Fernández JM, Ortiz Mellet C..  (2016)  Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.,  121  [PMID:26361824] [10.1016/j.ejmech.2015.08.038]

4. Kato A, Nakagome I, Kanekiyo U, Lu TT, Li YX, Yoshimura K, Kishida M, Shinzawa K, Yoshida T, Tanaka N, Jia YM, Nash RJ, Fleet GWJ, Yu CY..  (2022)  5-C-Branched Deoxynojirimycin: Strategy for Designing a 1-Deoxynojirimycin-Based Pharmacological Chaperone with a Nanomolar Affinity for Pompe Disease.,  65  (3.0): [PMID:35072486] [10.1021/acs.jmedchem.1c01673]

5. Wang JZ, Cheng B, Kato A, Kise M, Shimadate Y, Jia YM, Li YX, Fleet GWJ, Yu CY..  (2022)  Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.,  233  [PMID:35255314] [10.1016/j.ejmech.2022.114230]

6. Li HY, Lee NC, Chiu YT, Chang YW, Lin CC, Chou CL, Chien YH, Hwu WL, Cheng WC..  (2023)  Harnessing polyhydroxylated pyrrolidines as a stabilizer of acid alpha-glucosidase (GAA) to enhance the efficacy of enzyme replacement therapy in Pompe disease.,  78  [PMID:36542959] [10.1016/j.bmc.2022.117129]

Source

Source(1):

• Scientific Literature