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

• ChemBase ID: 133929
• Molecular Formular: C12H19NNaO13S
• Molecular Mass: 440.33293
• Monoisotopic Mass: 440.04747995
• SMILES: C1=C(OC(C(C1O)O)OC(C(COS(=O)(=O)O)O)C(C(C=O)N)O)C(=O)O.[Na]
• Canonical SMILES: O=CC(C(C(C(COS(=O)(=O)O)O)OC1OC(=CC(C1O)O)C(=O)O)O)N.[Na]
• InChI: InChI=1S/C12H19NO13S.Na/c13-4(2-14)8(17)10(6(16)3-24-27(21,22)23)26-12-9(18)5(15)1-7(25-12)11(19)20;/h1-2,4-6,8-10,12,15-18H,3,13H2,(H,19,20)(H,21,22,23)
• InChIKey: PZZOMOYPUZNPJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 136098-02-7
• MDL Number: MFCD00466929
• PubChem SID: 162228206; 24895838
• PubChem CID: 16219490

CALCULATED PROPERTIES

• Acid pKa: -1.861492
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -7.9705424
• LogD (pH = 7.4): -9.323788
• Log P: -5.347914
• Molar Refractivity: 81.6366 cm^3
• Polarizability: 33.925026 Å^3
• Polar Surface Area: 243.37 Å^2
• Rotatable Bonds: 10
• 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 - H9017

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.