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

• ChemBase ID: 134249
• Molecular Formular: C12H19NO10
• Molecular Mass: 337.27996
• Monoisotopic Mass: 337.10089581
• SMILES: C1=C(OC(C(C1O)O)OC(C(CO)O)C(C(C=O)N)O)C(=O)O
• Canonical SMILES: OCC(C(C(C(C=O)N)O)OC1OC(=CC(C1O)O)C(=O)O)O
• InChI: InChI=1S/C12H19NO10/c13-4(2-14)8(18)10(6(17)3-15)23-12-9(19)5(16)1-7(22-12)11(20)21/h1-2,4-6,8-10,12,15-19H,3,13H2,(H,20,21)
• InChIKey: RSCSYLOUHOXZCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 123228-39-7
• MDL Number: MFCD00166787
• PubChem SID: 162228526; 24895848
• PubChem CID: 5056205

CALCULATED PROPERTIES

• Acid pKa: 3.0664406
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -6.653359
• LogD (pH = 7.4): -7.043536
• Log P: -6.650121
• Molar Refractivity: 71.6448 cm^3
• Polarizability: 28.924925 Å^3
• Polar Surface Area: 200.0 Å^2
• Rotatable Bonds: 8
• 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

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - H9276

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.