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
Associated Targets(Human)
Glycogen debranching enzyme 27 Activities
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Beta-glucocerebrosidase 14647 Activities
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Sucrase-isomaltase 84 Activities
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Lysosomal alpha-glucosidase 35701 Activities
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Beta-glucosidase cytosolic 63 Activities
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Associated Targets(non-human)
Sucrase-isomaltase 908 Activities
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Beta-galactosidase 500 Activities
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Glucosylceramidase 58 Activities
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Uncharacterized protein 99 Activities
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Trehalase 42 Activities
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Lactase-glycosylceramidase 87 Activities
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Acidic alpha-glucosidase 551 Activities
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Alpha-mannosidase 234 Activities
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Alpha-galactosidase 362 Activities
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Beta-galactosidase 85 Activities
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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
Drug Indications
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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]