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

• ChemBase ID: 133010
• Molecular Formular: C14H21NNaO11
• Molecular Mass: 402.30641
• Monoisotopic Mass: 402.10122978
• SMILES: CC(=O)NC(C=O)C(C(C(CO)O)OC1C(C(C=C(O1)C(=O)O)O)O)O.[Na]
• Canonical SMILES: OCC(C(C(C(NC(=O)C)C=O)O)OC1OC(=CC(C1O)O)C(=O)O)O.[Na]
• InChI: InChI=1S/C14H21NO11.Na/c1-5(18)15-6(3-16)10(21)12(8(20)4-17)26-14-11(22)7(19)2-9(25-14)13(23)24;/h2-3,6-8,10-12,14,17,19-22H,4H2,1H3,(H,15,18)(H,23,24)
• InChIKey: PSTYFKXNCPXGDR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy]-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid sodium
• IUPAC Traditional name: 6-[(5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl)oxy]-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid sodium
• Synonyms: α-ΔUA-[1→4]-GlcNAc; Heparin disaccharide IV-A sodium salt

Database IDs

• CAS Number: 136098-07-2
• MDL Number: MFCD00466934
• PubChem SID: 24895417; 162227287
• PubChem CID: 16219466

CALCULATED PROPERTIES

• Acid pKa: 3.324201
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -6.727893
• LogD (pH = 7.4): -7.9889297
• Log P: -4.568028
• Molar Refractivity: 81.0886 cm^3
• Polarizability: 32.36584 Å^3
• Polar Surface Area: 203.08 Å^2
• Rotatable Bonds: 9
• 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 - H0895

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 and III