(4R,5S)-5-{[(2R,4R,5S)-5-{[(2R,4S,5S)-3,4-dihydroxy-6-methyl-5-{[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: 158826
• Molecular Formular: C25H43NO18
• Molecular Mass: 645.60482
• Monoisotopic Mass: 645.24801354
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)O)O)O[C@H]1OC([C@H]([C@@H](C1O)O)O[C@H]1OC([C@H]([C@@H](C1O)O)NC1C(C(C(C(=C1)CO)O)O)O)C)CO
• Canonical SMILES: OCC1O[C@H](O[C@@H]2C(CO)OC(C([C@H]2O)O)O)C([C@H]([C@@H]1O[C@H]1OC(C)[C@H]([C@@H](C1O)O)NC1C=C(CO)C(C(C1O)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-ASLBNVDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-5-{[(2R,4R,5S)-5-{[(2R,4S,5S)-3,4-dihydroxy-6-methyl-5-{[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: (4R,5S)-5-{[(2R,4R,5S)-5-{[(2R,4S,5S)-3,4-dihydroxy-6-methyl-5-{[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: O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucose; Arcabose; Ascarbose; BAY-g 5421; Glucobay; Prandase; Precose; Acarbose

Database IDs

• CAS Number: 56180-94-0
• PubChem SID: 162252961
• PubChem CID: 71312704

CALCULATED PROPERTIES

• 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
• Acid pKa: 11.225573

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 165-170°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A123500

Used as an anti-diabetic.

REFERENCES

• Sailor, D., et al.: Arzneimittel-Forshc., 30, 2182 (1981)