80312-32-9 , 4-O-(a-D-Glucopyranosyl) moranoline ,
G1M; 4-O-(a-D-Glucopyranosyl)-1-deoxynojirimycin
C12H23NO9 / 325.32
MFCD00269997
4-O-(a-D-Glucopyranosyl)-1-deoxynojirimycin
Moranoline is a metabolite of moranoline, a monosaccharide that is found in the leaves of Moraceae plants. Moranoline has been reported to have anti-inflammatory and anti-nociceptive effects in animal models, as well as an inhibitory effect on the release of proinflammatory cytokines.
4-O-alpha-D-glucopyranosylmoranoline is a monosaccharide derivative that is (2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol having an alpha-D-glucosyl residue attached at position 4. It has a role as a metabolite. It is a monosaccharide derivative and an alpha-D-glucoside. It derives from an alpha-D-glucose and a duvoglustat.
Glucopyranosylmoranoline belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Glucopyranosylmoranoline is soluble (in water) and a very weakly acidic compound (based on its pKa). Glucopyranosylmoranoline can be biosynthesized from alpha-D-glucose and duvoglustat.
CAS Number | 80312-32-9 |
Product Name | 4-O-alpha-D-Glucopyranosylmoranoline |
IUPAC Name | (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C12H23NO9 |
Molecular Weight | 325.31 g/mol |
InChI | InChI=1S/C12H23NO9/c14-2-4-11(7(17)5(16)1-13-4)22-12-10(20)9(19)8(18)6(3-15)21-12/h4-20H,1-3H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-/m1/s1 |
InChI Key | GNVIYGFSOIHFHK-NIKVEEOSSA-N |
SMILES | C1C(C(C(C(N1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O |
Synonyms | 1-deoxy-nojirimycin 4-O-alpha-D-glucopyranose, 1-deoxynojirimycin 4-O-alpha-D-glucopyranose, 4-O-alpha-D-glucopyranosylmoranoline, 4-O-glucopyranosylmoranoline, MOR-502 |
Canonical SMILES | C1C(C(C(C(N1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O |
Isomeric SMILES | C1[C@@H]([C@H]([C@@H]([C@H](N1)CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O |
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