trisodium (2R,3S,4S,5R,6R)-6-{[(2R,3S,4S,5S)-5-formyl-4-hydroxy-2-[(sulfonatooxy)methyl]oxolan-3-yl]oxy}-3,4-dihydroxy-5-(sulfonatooxy)oxane-2-carboxylate

• ChemBase ID: 171513
• Molecular Formular: C12H15Na3O17S2
• Molecular Mass: 564.33661
• Monoisotopic Mass: 563.94437386
• SMILES: [C@@H]1([C@H]([C@@H]([C@@H]([C@@H](O1)O[C@@H]1[C@H](O[C@@H]([C@@H]1O)C=O)COS(=O)(=O)[O-])OS(=O)(=O)[O-])O)O)C(=O)[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: O=C[C@H]1O[C@@H]([C@H]([C@H]1O)O[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1OS(=O)(=O)[O-])O)O)COS(=O)(=O)[O-].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C12H18O17S2.3Na/c13-1-3-5(14)8(4(26-3)2-25-30(19,20)21)27-12-10(29-31(22,23)24)7(16)6(15)9(28-12)11(17)18;;;/h1,3-10,12,14-16H,2H2,(H,17,18)(H,19,20,21)(H,22,23,24);;;/q;3*+1/p-3/t3-,4-,5-,6+,7+,8-,9-,10-,12-;;;/m1.../s1
• InChIKey: RUHOTWOTDGWTAC-VKWYMCEUSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (2R,3S,4S,5R,6R)-6-{[(2R,3S,4S,5S)-5-formyl-4-hydroxy-2-[(sulfonatooxy)methyl]oxolan-3-yl]oxy}-3,4-dihydroxy-5-(sulfonatooxy)oxane-2-carboxylate
• IUPAC Traditional name: trisodium (2R,3S,4S,5R,6R)-6-{[(2R,3S,4S,5S)-5-formyl-4-hydroxy-2-[(sulfonatooxy)methyl]oxolan-3-yl]oxy}-3,4-dihydroxy-5-(sulfonatooxy)oxane-2-carboxylate
• Synonyms: 2,5-Anhydro-4-O-(2-O-sulfo-α-L-idopyranuronosyl)-D-mannose 6-(Hydrogen Sulfate); O-(α-L-Idopyranosyluronic Acid 2-Sulfate-(1-4)-2,5-anhydromannose-6-sulfate Trisodium Salt, 90%

Database IDs

• PubChem SID: 164227423
• PubChem CID: 71749446

CALCULATED PROPERTIES

• Acid pKa: -2.4100256
• H Acceptors: 15
• H Donor: 3
• LogD (pH = 5.5): -11.142608
• LogD (pH = 7.4): -11.994249
• Log P: -7.596947
• Molar Refractivity: 94.6935 cm^3
• Polarizability: 37.466232 Å^3
• Polar Surface Area: 278.44 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 205-207°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I192700

A sulfated oligosaccharide isolated from the deamination products of Heparins.

REFERENCES

• Delaney, S.R., et al.: Biochem. J., 209, 315 (1983)