2,6-Bis-hydroxymethyl-piperidine-3,4,5-triol

ID: ALA501355

Chembl Id: CHEMBL501355

Max Phase: Preclinical

Molecular Formula: C7H15NO5

Molecular Weight: 193.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Alpha-Homonojirimycin

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

Standard InChI:  InChI=1S/C7H15NO5/c9-1-3-5(11)7(13)6(12)4(2-10)8-3/h3-13H,1-2H2/t3-,4-,5-,6+,7+/m1/s1

Standard InChI Key:  CLVUFWXGNIFGNC-OVHBTUCOSA-N

Alternative Forms

1. Parent:

   

   ALA501355

   ---

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: 193.20

Molecular Weight (Monoisotopic): 193.0950

AlogP: -3.61

#Rotatable Bonds: 2

Polar Surface Area: 113.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.84

CX Basic pKa: 7.60

CX LogP: -3.52

CX LogD: -3.93

Aromatic Rings: 0

Heavy Atoms: 13

QED Weighted: 0.27

Np Likeness Score: 1.84

References

1. Asano N, Nishida M, Kato A, Kizu H, Matsui K, Shimada Y, Itoh T, Baba M, Watson AA, Nash RJ, Lilley PM, Watkin DJ, Fleet GW..  (1998)  Homonojirimycin isomers and N-alkylated homonojirimycins: structural and conformational basis of inhibition of glycosidases.,  41  (14): [PMID:9651160] [10.1021/jm970836l]

2. Martin OR, Compain P, Kizu H, Asano N..  (1999)  Revised structure of a homonojirimycin isomer from Aglaonema treubii: first example of a naturally occurring alpha-homoallonojirimycin.,  9  (21): [PMID:10560746] [10.1016/s0960-894x(99)00551-x]

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. Kuriyama C, Kamiyama O, Ikeda K, Sanae F, Kato A, Adachi I, Imahori T, Takahata H, Okamoto T, Asano N..  (2008)  In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.,  16  (15): [PMID:18595718] [10.1016/j.bmc.2008.06.026]

5. Yan RY, Wang HQ, Liu C, Kang J, Chen RY..  (2013)  α-Glucosidase-inhibitory iminosugars from the leaves of Suregada glomerulata.,  21  (21): [PMID:23993676] [10.1016/j.bmc.2013.07.048]

6.  (2015)  Method for the treatment of pompe disease using 1-deoxynojirimycin and derivatives, 

Source

Source(2):

• Scientific Literature
• BindingDB Database