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

• ChemBase ID: 132483
• Molecular Formular: C12H19NNaO16S2
• Molecular Mass: 520.39613
• Monoisotopic Mass: 520.00429481
• SMILES: C1=C(OC(C(C1O)O)OC(C(COS(=O)(=O)O)O)C(C(C=O)NS(=O)(=O)O)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)NS(=O)(=O)O.[Na]
• InChI: InChI=1S/C12H19NO16S2.Na/c14-2-4(13-30(21,22)23)8(17)10(6(16)3-27-31(24,25)26)29-12-9(18)5(15)1-7(28-12)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: YSFOXIFCPZNBSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 136098-05-0
• MDL Number: MFCD00466930
• PubChem SID: 162226760; 24895423
• PubChem CID: 16219467

CALCULATED PROPERTIES

• Acid pKa: -2.2153478
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -12.167998
• LogD (pH = 7.4): -13.13875
• Log P: -8.257063
• 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 - H1020

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 II