2,5-dideoxy-2,5-imino-L-mannitol

ID: ALA405957

Chembl Id: CHEMBL405957

Cas Number: 219562-44-4

PubChem CID: 11073745

Max Phase: Preclinical

Molecular Formula: C6H13NO4

Molecular Weight: 163.17

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5-,6-/m0/s1

Standard InChI Key:  PFYHYHZGDNWFIF-BXKVDMCESA-N

Alternative Forms

1. Parent:

   

   ALA405957

   (2S,3S,4S,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol

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: 163.17

Molecular Weight (Monoisotopic): 163.0845

AlogP: -2.97

#Rotatable Bonds: 2

Polar Surface Area: 92.95

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.18

CX Basic pKa: 8.88

CX LogP: -2.89

CX LogD: -4.38

Aromatic Rings: 0

Heavy Atoms: 11

QED Weighted: 0.30

Np Likeness Score: 1.93

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. Miyawaki S, Hirokami Y, Kinami K, Hoshino M, Minehira D, Miyamoto D, Nash RJ, Fleet GW, Adachi I, Toyooka N, Kato A..  (2017)  Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.,  25  (1): [PMID:27789075] [10.1016/j.bmc.2016.10.015]

4. 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