disodium (2R,3S,4S,5R,6R)-6-{[(2R,3S,4R,5R,6S)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxy-5-(sulfonatooxy)oxane-2-carboxylate

• ChemBase ID: 171512
• Molecular Formular: C14H21NNa2O15S
• Molecular Mass: 521.35878
• Monoisotopic Mass: 521.04272854
• SMILES: [C@@H]1([C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H]([C@H](O[C@H]1CO)O)NC(=O)C)O)OS(=O)(=O)[O-])O)O)C(=O)[O-].[Na+].[Na+]
• Canonical SMILES: OC[C@@H]1O[C@H](O)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@H]1OS(=O)(=O)[O-])O)O)O)NC(=O)C.[Na+].[Na+]
• InChI: InChI=1S/C14H23NO15S.2Na/c1-3(17)15-5-6(18)9(4(2-16)27-13(5)23)28-14-11(30-31(24,25)26)8(20)7(19)10(29-14)12(21)22;;/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26);;/q;2*+1/p-2/t4-,5-,6-,7+,8+,9-,10-,11-,13+,14-;;/m1../s1
• InChIKey: CGOPPDPSPPSBHE-FQHXJEBZSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R,3S,4S,5R,6R)-6-{[(2R,3S,4R,5R,6S)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxy-5-(sulfonatooxy)oxane-2-carboxylate
• IUPAC Traditional name: disodium (2R,3S,4S,5R,6R)-6-{[(2R,3S,4R,5R,6S)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxy-5-(sulfonatooxy)oxane-2-carboxylate
• Synonyms: 2-(Acetylamino)-2-deoxy-4-O-(2-O-sulfo-α-L-idopyranuronosyl)-α-D-Glucopyranose Disodium Salt; O-(α-L-Idopyranosyluronic Acid 2-Sulfate-(1-4)-N-acetylglucosamine Disodium Salt

Database IDs

• PubChem SID: 164227422
• PubChem CID: 71749444

CALCULATED PROPERTIES

• Acid pKa: -1.92446
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -9.4549265
• LogD (pH = 7.4): -10.467152
• Log P: -6.414805
• Molar Refractivity: 99.0126 cm^3
• Polarizability: 38.020916 Å^3
• Polar Surface Area: 264.5 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I192600

A Heparin sulfate analogue as a Novel β-Secretase ιnhibitor as potential Alzheimer's disease therapeutics.

REFERENCES

• Scholefield, Z., et al.: J. Cell Biol., 163, 97 (2003)
• Patey, S., et al.: J. Med. Chem., 49, 6129 (2003)
• Rudd, T., et al.: Glycobiology, 17, 983 (2003)