4-hydroxy-3-(sulfooxy)-2-{[1,2,4-trihydroxy-6-oxo-5-(sulfoamino)hexan-3-yl]oxy}-3,4-dihydro-2H-pyran-6-carboxylic acid sodium

• ChemBase ID: 134267
• Molecular Formular: C12H19NNaO16S2
• Molecular Mass: 520.39613
• Monoisotopic Mass: 520.00429481
• SMILES: C1=C(OC(C(C1O)OS(=O)(=O)O)OC(C(CO)O)C(C(C=O)NS(=O)(=O)O)O)C(=O)O.[Na]
• Canonical SMILES: OCC(C(C(C(NS(=O)(=O)O)C=O)O)OC1OC(=CC(C1OS(=O)(=O)O)O)C(=O)O)O.[Na]
• InChI: InChI=1S/C12H19NO16S2.Na/c14-2-4(13-30(21,22)23)8(18)9(6(17)3-15)28-12-10(29-31(24,25)26)5(16)1-7(27-12)11(19)20;/h1-2,4-6,8-10,12-13,15-18H,3H2,(H,19,20)(H,21,22,23)(H,24,25,26)
• InChIKey: BXIKJIZZPZSIFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-(sulfooxy)-2-{[1,2,4-trihydroxy-6-oxo-5-(sulfoamino)hexan-3-yl]oxy}-3,4-dihydro-2H-pyran-6-carboxylic acid sodium
• IUPAC Traditional name: 4-hydroxy-5-(sulfooxy)-6-{[1,2,4-trihydroxy-6-oxo-5-(sulfoamino)hexan-3-yl]oxy}-5,6-dihydro-4H-pyran-2-carboxylic acid sodium
• Synonyms: α-ΔUA-2S-[1→4]-GlcNS; Heparin disaccharide III-S sodium salt

Database IDs

• CAS Number: 136098-03-8
• MDL Number: MFCD00466933
• PubChem SID: 162228544; 24895854
• PubChem CID: 16219495

CALCULATED PROPERTIES

• Acid pKa: -2.098623
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -12.22092
• LogD (pH = 7.4): -13.144604
• Log P: -8.15111
• Molar Refractivity: 91.9207 cm^3
• Polarizability: 38.706993 Å^3
• Polar Surface Area: 283.75 Å^2
• Rotatable Bonds: 11
• 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

DETAILS

Sigma Aldrich - H9392

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.
Preparation Note
Produced by the action of heparinase I and II