5-({5-[(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-[hydroxy(2H2)methyl]oxan-2-yl}oxy)-6-[hydroxy(2H2)methyl]oxane-2,3,4-triol

• ChemBase ID: 158827
• Molecular Formular: C25H43NO18
• Molecular Mass: 645.60482
• Monoisotopic Mass: 645.24801354
• SMILES: C1(C(C(C(OC1CO)O)O)O)OC1OC(C(C(C1O)O)OC1OC(C(C(C1O)O)NC1C(C(C(C(=C1)CO)O)O)O)C)CO
• Canonical SMILES: OCC1OC(OC2C(CO)OC(C(C2O)O)O)C(C(C1OC1OC(C)C(C(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
• InChIKey: XUFXOAAUWZOOIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-({5-[(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-[hydroxy(^2H₂)methyl]oxan-2-yl}oxy)-6-[hydroxy(^2H₂)methyl]oxane-2,3,4-triol
• IUPAC Traditional name: 5-({5-[(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-[hydroxy(^2H₂)methyl]oxan-2-yl}oxy)-6-[hydroxy(^2H₂)methyl]oxane-2,3,4-triol
• Synonyms: O-4,6-Dideoxy-4-[[[1S-(1α,4α,5β,6α)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-D-glucose-d4; Glucobay-d4; Prandase-d4; Precose-d4; Acarbose-d4

Database IDs

• PubChem SID: 162252962
• PubChem CID: 45038073

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

Physical Property

• Solubility: Water
• Apperance: Amorphous Powder

DETAILS

Toronto Research Chemicals - A123502

Used as an antidiabetic.

REFERENCES

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