2-[(5-amino-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy]-4-hydroxy-3-(sulfooxy)-3,4-dihydro-2H-pyran-6-carboxylic acid sodium

• ChemBase ID: 132482
• Molecular Formular: C12H19NNaO13S
• Molecular Mass: 440.33293
• Monoisotopic Mass: 440.04747995
• SMILES: C1=C(OC(C(C1O)OS(=O)(=O)O)OC(C(CO)O)C(C(C=O)N)O)C(=O)O.[Na]
• Canonical SMILES: OCC(C(C(C(C=O)N)O)OC1OC(=CC(C1OS(=O)(=O)O)O)C(=O)O)O.[Na]
• InChI: InChI=1S/C12H19NO13S.Na/c13-4(2-14)8(18)9(6(17)3-15)25-12-10(26-27(21,22)23)5(16)1-7(24-12)11(19)20;/h1-2,4-6,8-10,12,15-18H,3,13H2,(H,19,20)(H,21,22,23)
• InChIKey: FMUFFQOUMUSRRU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 136098-01-6
• MDL Number: MFCD00466932
• PubChem SID: 24895842; 162226759
• PubChem CID: 16219492

CALCULATED PROPERTIES

• Acid pKa: -1.8553355
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -8.047592
• LogD (pH = 7.4): -9.331895
• Log P: -5.348138
• 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 - H9142

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.