trisodium (2R,3R,4S)-2-{[(2R,3S,4R,5R)-5-amino-4,6-dihydroxy-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-4-hydroxy-3-(sulfonatooxy)-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 155205
• Molecular Formular: C12H16NNa3O16S2
• Molecular Mass: 563.35185
• Monoisotopic Mass: 562.96035828
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1O)OS(=O)(=O)[O-])O[C@@H]1[C@H](OC([C@@H]([C@H]1O)N)O)COS(=O)(=O)[O-])C(=O)[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@H]1C=C(O[C@H]([C@@H]1OS(=O)(=O)[O-])O[C@@H]1[C@@H](COS(=O)(=O)[O-])OC([C@@H]([C@H]1O)N)O)C(=O)[O-].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C12H19NO16S2.3Na/c13-6-7(15)9(5(26-11(6)18)2-25-30(19,20)21)28-12-8(29-31(22,23)24)3(14)1-4(27-12)10(16)17;;;/h1,3,5-9,11-12,14-15,18H,2,13H2,(H,16,17)(H,19,20,21)(H,22,23,24);;;/q;3*+1/p-3/t3-,5+,6+,7+,8+,9+,11?,12-;;;/m0.../s1
• InChIKey: WHYGSGRAJJCXLY-LXROVJCJSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (2R,3R,4S)-2-{[(2R,3S,4R,5R)-5-amino-4,6-dihydroxy-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-4-hydroxy-3-(sulfonatooxy)-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: trisodium (4S,5R,6R)-6-{[(2R,3S,4R,5R)-5-amino-4,6-dihydroxy-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-4-hydroxy-5-(sulfonatooxy)-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: α-ΔUA-2S-[1→4]-GlcN-6S; Heparin disaccharide I-H sodium salt

Database IDs

• CAS Number: 136098-04-9
• MDL Number: MFCD00466926
• PubChem SID: 162249343
• PubChem CID: 71312100

CALCULATED PROPERTIES

• Acid pKa: -2.3258324
• H Acceptors: 15
• H Donor: 4
• LogD (pH = 5.5): -9.908029
• LogD (pH = 7.4): -10.661542
• Log P: -6.2964897
• Molar Refractivity: 98.7999 cm^3
• Polarizability: 38.495884 Å^3
• Polar Surface Area: 287.39 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Linear Formula: C12H17NO16S2Na2

DETAILS

Sigma Aldrich - H8892

Biochem/physiol Actions
Products of the digestion of heparin and heparan sulfate by various heparinases
Other Notes
In the following listings, ΔUA = 4-deoxy-L-threo-hex-4-enopyranosyluronic acid; GlcN = D-glucosamine; Ac = Acetyl; NS, 2S, 6S, = N-sulfo, 2-sulfate and 6-sulfate respectively.