2-Hydroxymethyl-piperidine-3,4-diol

ID: ALA456583

Chembl Id: CHEMBL456583

Cas Number: 156639-77-9

PubChem CID: 10290867

Max Phase: Preclinical

Molecular Formula: C6H13NO3

Molecular Weight: 147.17

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-Epi-Fagomine | 3-Epifagomine | 3-epi-fagomine|3-Epifagomine|CHEMBL456583|(2R,3R,4S)-2-(hydroxymethyl)piperidine-3,4-diol|156639-77-9|CHEBI:132399|DTXSID001317313|BDBM50292389|AKOS006352899|Q27225561

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

Standard InChI:  InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5+,6-/m1/s1

Standard InChI Key:  YZNNBIPIQWYLDM-NGJCXOISSA-N

Alternative Forms

1. Parent:

   

   ALA456583

   3-Epi-fagomine

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: 147.17

Molecular Weight (Monoisotopic): 147.0895

AlogP: -1.94

#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: 13.43

CX Basic pKa: 8.63

CX LogP: -2.20

CX LogD: -3.45

Aromatic Rings: 0

Heavy Atoms: 10

QED Weighted: 0.35

Np Likeness Score: 2.96

References

1. Asano N, Oseki K, Kizu H, Matsui K..  (1994)  Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.,  37  (22): [PMID:7966130] [10.1021/jm00048a006]

2. Kato A, Asano N, Kizu H, Matsui K..  (1997)  Fagomine isomers and glycosides from Xanthocercis zambesiaca.,  60  (3): [PMID:9157194] [10.1021/np960646y]

3. Nojima H, Kimura I, Chen FJ, Sugihara Y, Haruno M, Kato A, Asano N..  (1998)  Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.,  61  (3): [PMID:9544568] [10.1021/np970277l]

4. Kato A, Miyauchi S, Kato N, Nash RJ, Yoshimura Y, Nakagome I, Hirono S, Takahata H, Adachi I..  (2011)  Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.,  19  (11): [PMID:21546253] [10.1016/j.bmc.2011.04.011]

5. van den Berg RJ, Wennekes T, Ghisaidoobe A, Donker-Koopman WE, Strijland A, Boot RG, van der Marel GA, Aerts JM, Overkleeft HS..  (2011)  Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors.,  2  (7): [PMID:24900342] [10.1021/ml200050s]

6. 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]

Source

Source(1):

• Scientific Literature