(2R,3R,4R,5R)-2,5-Bis-hydroxymethyl-pyrrolidine-3,4-diol

ID: ALA312653

Chembl Id: CHEMBL312653

Cas Number: 59920-31-9

PubChem CID: 124702

Product Number: D130950

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-/m1/s1

Standard InChI Key:  PFYHYHZGDNWFIF-KVTDHHQDSA-N

Alternative Forms

1. Parent:

   

   ALA312653

   2,5-Dideoxy-2,5-imino-D-mannitol

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. Asano N, Kizu H, Oseki K, Tomioka E, Matsui K, Okamoto M, Baba M..  (1995)  N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.,  38  (13): [PMID:7608901] [10.1021/jm00013a012]

2. 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]

3. 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]

4. Yasuda K, Kizu H, Yamashita T, Kameda Y, Kato A, Nash RJ, Fleet GW, Molyneux RJ, Asano N..  (2002)  New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii.,  65  (2): [PMID:11858756] [10.1021/np010360f]

5. 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]

6. Asano N, Kato A, Miyauchi M, Kizu H, Kameda Y, Watson AA, Nash RJ, Fleet GW..  (1998)  Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.,  61  (5): [PMID:9599261] [10.1021/np9705726]

7. Molyneux RJ, Pan YT, Tropea JE, Elbein AD, Lawyer CH, Hughes DJ, Fleet GW..  (1993)  2-Hydroxymethyl-3,4-dihydroxy-6-methyl-pyrrolidine (6-deoxy-DMDP), an alkaloid beta-mannosidase inhibitor from seeds of Angylocalyx pynaertii.,  56  (8): [PMID:8229017] [10.1021/np50098a020]

8. Pototschnig G, De Csáky CM, Burke JR, Schitter G, Stütz AE, Tarling CA, Withers SG, Wrodnigg TM..  (2010)  Synthesis and biological evaluation of novel biotin-iminoalditol conjugates.,  20  (14): [PMID:20610152] [10.1016/j.bmcl.2010.05.084]

9. Wang J, Lin T, Chen Y, Lin C, Fang J.  (2013)  Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors,  4  (5): [10.1039/C3MD00033H]

10. 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]

11. 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