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

• ChemBase ID: 131039
• Molecular Formular: C15H23NNaO17S2
• Molecular Mass: 576.45939
• Monoisotopic Mass: 576.03050956
• SMILES: CCC(=O)NC(C=O)C(C(C(COS(=O)(=O)O)O)OC1C(C(C=C(O1)C(=O)O)O)OS(=O)(=O)O)O.[Na]
• Canonical SMILES: CCC(=O)NC(C(C(C(COS(=O)(=O)O)O)OC1OC(=CC(C1OS(=O)(=O)O)O)C(=O)O)O)C=O.[Na]
• InChI: InChI=1S/C15H23NO17S2.Na/c1-2-10(20)16-6(4-17)11(21)12(8(19)5-30-34(24,25)26)32-15-13(33-35(27,28)29)7(18)3-9(31-15)14(22)23;/h3-4,6-8,11-13,15,18-19,21H,2,5H2,1H3,(H,16,20)(H,22,23)(H,24,25,26)(H,27,28,29)
• InChIKey: AFUHZNWLJKMBCR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[2,4-dihydroxy-6-oxo-5-propanamido-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-propanamido-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]-GlcNCOEt-6S); Heparin disaccharide I-P sodium salt

Database IDs

• CAS Number: 149368-05-8
• MDL Number: MFCD00166872
• PubChem SID: 162225317
• PubChem CID: 71308379

CALCULATED PROPERTIES

• Acid pKa: -2.3376586
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -11.096654
• LogD (pH = 7.4): -11.9992075
• Log P: -7.5105515
• Molar Refractivity: 105.6991 cm^3
• Polarizability: 44.1706 Å^3
• Polar Surface Area: 289.82 Å^2
• Rotatable Bonds: 14
• 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

DETAILS

Sigma Aldrich - H9401

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.