ID: ALA406973

Max Phase: Preclinical

Molecular Formula: C5H11NO3

Molecular Weight: 133.15

Molecule Type: Small molecule

Associated Items:

Representations

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

Associated Targets(Human)

Glycogen debranching enzyme 27 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Beta-glucocerebrosidase 14647 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Sucrase-isomaltase 84 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Lysosomal alpha-glucosidase 35701 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Beta-glucosidase cytosolic 63 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Sucrase-isomaltase 908 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Beta-galactosidase 500 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Glucosylceramidase 58 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Uncharacterized protein 99 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Trehalase 42 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Lactase-glycosylceramidase 87 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Acidic alpha-glucosidase 551 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Alpha-mannosidase 234 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Alpha-galactosidase 362 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Beta-galactosidase 85 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 133.15Molecular Weight (Monoisotopic): 133.0739AlogP: -2.33#Rotatable Bonds: 1
Polar Surface Area: 72.72Molecular Species: BASEHBA: 4HBD: 4
#RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 4#RO5 Violations (Lipinski): 0
CX Acidic pKa: 13.32CX Basic pKa: 9.36CX LogP: -2.26CX LogD: -4.20
Aromatic Rings: 0Heavy Atoms: 9QED Weighted: 0.32Np 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