ID: ALA175901

Max Phase: Preclinical

Molecular Formula: C6H13NO4

Molecular Weight: 163.17

Molecule Type: Small molecule

Representations

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

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

Standard InChI Key:  LXBIFEVIBLOUGU-UNTFVMJOSA-N

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

Properties

Molecular Weight: 163.17

Molecular Weight (Monoisotopic): 163.0845

AlogP: -2.97

#Rotatable Bonds: 1

Polar Surface Area: 92.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.91

CX Basic pKa: 8.06

CX LogP: -2.89

CX LogD: -3.63

Aromatic Rings: 0

Heavy Atoms: 11

QED Weighted: 0.28

Np Likeness Score: 2.44

References

1. Kato A, Kato N, Kano E, Adachi I, Ikeda K, Yu L, Okamoto T, Banba Y, Ouchi H, Takahata H, Asano N..  (2005)  Biological properties of D- and L-1-deoxyazasugars.,  48  (6): [PMID:15771446] [10.1021/jm0495881]

2. Wennekes T, Meijer AJ, Groen AK, Boot RG, Groener JE, van Eijk M, Ottenhoff R, Bijl N, Ghauharali K, Song H, O'Shea TJ, Liu H, Yew N, Copeland D, van den Berg RJ, van der Marel GA, Overkleeft HS, Aerts JM..  (2010)  Dual-action lipophilic iminosugar improves glycemic control in obese rodents by reduction of visceral glycosphingolipids and buffering of carbohydrate assimilation.,  53  (2): [PMID:20000679] [10.1021/jm901281m]

3. 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]

4. Lu TT, Shimadate Y, Cheng B, Kanekiyo U, Kato A, Wang JZ, Li YX, Jia YM, Fleet GWJ, Yu CY..  (2021)  Synthesis and glycosidase inhibition of 5-C-alkyl-DNJ and 5-C-alkyl-l-ido-DNJ derivatives.,  224  [PMID:34340042] [10.1016/j.ejmech.2021.113716]

5. 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]

Source

Source(1):

• Scientific Literature