(3R,4R,6R)-5-{[(3R,4R,6R)-5-{[(3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol

• ChemBase ID: 179847
• Molecular Formular: C25H43NO18
• Molecular Mass: 645.60482
• Monoisotopic Mass: 645.24801354
• SMILES: C1([C@@H]([C@@H](C(OC2[C@@H]([C@@H]([C@H](N[C@@H]3[C@H]([C@H]([C@@H](C(=C3)CO)O)O)O)[C@H](O2)C)O)O)[C@H](O1)CO)O)O)OC1[C@H]([C@H](C(O[C@@H]1CO)O)O)O
• Canonical SMILES: OC[C@H]1OC(OC2[C@@H](CO)OC([C@@H]([C@@H]2O)O)O)[C@@H]([C@@H](C1OC1O[C@H](C)[C@H]([C@H]([C@H]1O)O)N[C@H]1C=C(CO)[C@H]([C@@H]([C@@H]1O)O)O)O)O
• InChI: InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12-,13+,14+,15+,16-,17-,18-,19-,20-,21?,22?,23?,24?,25?/m1/s1
• InChIKey: XUFXOAAUWZOOIT-XTKLSINSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,6R)-5-{[(3R,4R,6R)-5-{[(3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol
• IUPAC Traditional name: (3R,4R,6R)-5-{[(3R,4R,6R)-5-{[(3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol
• Synonyms: Amylostatin J; Glucobay; Precose; Prandase; Acarbose

Database IDs

• CAS Number: 56180-94-0
• PubChem SID: 164235757
• PubChem CID: 44891366

CALCULATED PROPERTIES

• Acid pKa: 11.225573
• H Acceptors: 19
• H Donor: 14
• LogD (pH = 5.5): -9.150389
• LogD (pH = 7.4): -7.7692995
• Log P: -7.6145587
• Molar Refractivity: 137.6024 cm^3
• Polarizability: 57.392616 Å^3
• Polar Surface Area: 321.17 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: A potent inhibitor of alpha-glucosidases and saccharases

Product Information

• Biological Source: Isol. from Actinoplanes sp.
• Application(s): Used for treatment of diabetes, hyperlipidaemia and obesity

REFERENCES

• Ger. Pat., 1975, 2 347 782; CA, 83, 56721s
• Schmidt, D.D. et al., Naturwissenschaften, 1977, 64, 535-536; 536-537, (isol, props)
• Truscheit, E. et al., Angew. Chem., Int. Ed., 1981, 20, 744-761, (rev)
• Creutzfeldt, W., Int. Congr. Ser. Excerpta Med., 1982, 594, (book)
• Junge, B. et al., Carbohydr. Res., 1984, 128, 235-268, (struct)
• Bock, K. et al., Carbohydr. Res., 1984, 132, 142-149, (conformn)
• Ogawa, S. et al., Chem. Comm., 1988, 605, (synth)
• Clissold, S.P. et al., Drugs, 1988, 35, 214, (rev, pharmacol)
• Maul, W. et al., Arzneim.-Forsch., 1989, 39, 1251-1253, (synth)
• Shibata, Y. et al., Carbohydr. Res., 1989, 189, 309-322, (synth)
• Peruche, B., Pharm. Ztg., 1992, 137, 30; 32; 34; 36, (rev)