decasodium (2R,3S,4S,5R,6R)-3-{[(3R,4R,5R,6R)-5-{[(2R,3R,5S,6S)-6-carboxylato-5-{[(3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoamino)-6-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-3,4-dihydroxyoxan-2-yl]oxy}-3-(sulfonatoamino)-4-(sulfonatooxy)-6-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-4-hydroxy-6-{[(2R,3S,5R)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-5-(sulfonatooxy)oxane-2-carboxylate

• ChemBase ID: 169351
• Molecular Formular: C31H43N3Na10O49S8
• Molecular Mass: 1728.08152
• Monoisotopic Mass: 1726.77077558
• SMILES: O1C([C@H](C([C@@H]([C@@H]1COS(=O)(=O)[O-])O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)C(=O)[O-])OC1O[C@H]([C@H]([C@@H]([C@@H]1NS(=O)(=O)[O-])OS(=O)(=O)[O-])O[C@@H]1O[C@H]([C@H](C([C@@H]1O)O)OC1O[C@H]([C@H]([C@@H]([C@@H]1NS(=O)(=O)[O-])O)O)COS(=O)(=O)[O-])C(=O)[O-])COS(=O)(=O)[O-])O)OS(=O)(=O)[O-])O)NS(=O)(=O)[O-])OC.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: COC1O[C@@H](COS(=O)(=O)[O-])[C@H](C([C@@H]1NS(=O)(=O)[O-])O)O[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@H]1OS(=O)(=O)[O-])O)OC1O[C@@H](COS(=O)(=O)[O-])[C@H]([C@@H]([C@@H]1NS(=O)(=O)[O-])OS(=O)(=O)[O-])O[C@@H]1O[C@@H](C(=O)[O-])[C@H](C([C@@H]1O)O)OC1O[C@@H](COS(=O)(=O)[O-])[C@H]([C@@H]([C@@H]1NS(=O)(=O)[O-])O)O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C31H53N3O49S8.10Na/c1-69-27-9(33-85(48,49)50)13(37)17(6(74-27)3-71-88(57,58)59)76-31-22(83-91(66,67)68)16(40)21(24(81-31)26(43)44)79-29-10(34-86(51,52)53)19(82-90(63,64)65)18(7(75-29)4-72-89(60,61)62)77-30-15(39)14(38)20(23(80-30)25(41)42)78-28-8(32-84(45,46)47)12(36)11(35)5(73-28)2-70-87(54,55)56;;;;;;;;;;/h5-24,27-40H,2-4H2,1H3,(H,41,42)(H,43,44)(H,45,46,47)(H,48,49,50)(H,51,52,53)(H,54,55,56)(H,57,58,59)(H,60,61,62)(H,63,64,65)(H,66,67,68);;;;;;;;;;/q;10*+1/p-10/t5-,6-,7-,8-,9-,10-,11-,12-,13?,14?,15-,16+,17-,18-,19-,20+,21+,22-,23+,24-,27?,28?,29?,30-,31-;;;;;;;;;;/m1........../s1
• InChIKey: XEKSTYNIJLDDAZ-OHQYIAGXSA-D

NAMES AND DATABASE IDS

Names

• IUPAC name: decasodium (2R,3S,4S,5R,6R)-3-{[(3R,4R,5R,6R)-5-{[(2R,3R,5S,6S)-6-carboxylato-5-{[(3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoamino)-6-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-3,4-dihydroxyoxan-2-yl]oxy}-3-(sulfonatoamino)-4-(sulfonatooxy)-6-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-4-hydroxy-6-{[(2R,3S,5R)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-5-(sulfonatooxy)oxane-2-carboxylate
• IUPAC Traditional name: decasodium (2R,3S,4S,5R,6R)-3-{[(3R,4R,5R,6R)-5-{[(2R,3R,5S,6S)-6-carboxylato-5-{[(3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoamino)-6-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-3,4-dihydroxyoxan-2-yl]oxy}-3-(sulfonatoamino)-4-(sulfonatooxy)-6-[(sulfonatooxy)methyl]oxan-2-yl]oxy}-4-hydroxy-6-{[(2R,3S,5R)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-5-(sulfonatooxy)oxane-2-carboxylate
• Synonyms: Methyl O-2-Deoxy-6-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl-(14)-O-β-D-glucopyranuronosyl-(14)-O-2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl-(14)-O-2-O-sulfo-α-L-idopyranuronosyl-(14)-2-deoxy-2-(sulfoamino)-α-D-glucopyranoside 6-(Hydrogen Sulfate) Decasodium Salt; Arixtra; Fondaparin Sodium; IC 85158; IC 851589; Org 31540; SR 90107A; Xantidar; Fondaparinux Sodium

Database IDs

• CAS Number: 114870-03-0
• PubChem SID: 162263483
• PubChem CID: 71316923

CALCULATED PROPERTIES

• Acid pKa: -2.9501638
• H Acceptors: 44
• H Donor: 9
• LogD (pH = 5.5): -29.490952
• LogD (pH = 7.4): -29.490992
• Log P: -10.479802
• Molar Refractivity: 268.547 cm^3
• Polarizability: 112.532684 Å^3
• Polar Surface Area: 833.78 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Powder (after lyophilisation)

DETAILS

Toronto Research Chemicals - F683500

Synthetic pentasaccharide corresponding to the anti-thrombin binding site of heparin. Anti-thrombotic.

REFERENCES

• Herbert, J.M., et al.: Cardiovasc. Drug Rev., 15, 1 (1997)
• Turpie, A.G.G., et al.: Expert Opin. Drug Saf., 4, 707 (1997)