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

• ChemBase ID: 133447
• Molecular Formular: C12H19NNaO19S3
• Molecular Mass: 600.45933
• Monoisotopic Mass: 599.96110967
• SMILES: C1=C(OC(C(C1O)OS(=O)(=O)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(C1OS(=O)(=O)O)O)C(=O)O)O)NS(=O)(=O)O.[Na]
• InChI: InChI=1S/C12H19NO19S3.Na/c14-2-4(13-33(20,21)22)8(17)9(6(16)3-29-34(23,24)25)31-12-10(32-35(26,27)28)5(15)1-7(30-12)11(18)19;/h1-2,4-6,8-10,12-13,15-17H,3H2,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)
• InChIKey: NQBRSLPUXDFPBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 136098-10-7
• MDL Number: MFCD00466927
• PubChem SID: 162227724; 24895847
• PubChem CID: 16219493

CALCULATED PROPERTIES

• Acid pKa: -2.5311334
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -14.669823
• LogD (pH = 7.4): -15.47774
• Log P: -10.28947
• Molar Refractivity: 101.9125 cm^3
• Polarizability: 43.7455 Å^3
• Polar Surface Area: 327.12 Å^2
• Rotatable Bonds: 13
• 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 - H9267

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