6-[(3R,4R,5R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanoic acid

• ChemBase ID: 163707
• Molecular Formular: C12H23NO6
• Molecular Mass: 277.31412
• Monoisotopic Mass: 277.15253746
• SMILES: [C@@H]1([C@@H]([C@H](CN(C1CO)CCCCCC(=O)O)O)O)O
• Canonical SMILES: OCC1N(CCCCCC(=O)O)C[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H23NO6/c14-7-8-11(18)12(19)9(15)6-13(8)5-3-1-2-4-10(16)17/h8-9,11-12,14-15,18-19H,1-7H2,(H,16,17)/t8?,9-,11-,12-/m1/s1
• InChIKey: KTNVTDIFZTZBJY-WADXITAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(3R,4R,5R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanoic acid
• IUPAC Traditional name: 6-[(3R,4R,5R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanoic acid
• Synonyms: (2R,3R,4R,5S)-3,4,5-Trihydroxy-2-(hydroxymethyl)-1-piperidinehexanoic Acid; N-5-Carboxypentyl-1-deoxynojirimycin

Database IDs

• CAS Number: 79206-51-2
• PubChem SID: 162257842
• PubChem CID: 46780183

CALCULATED PROPERTIES

• Acid pKa: 3.932996
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.3429475
• LogD (pH = 7.4): -4.3677692
• Log P: -4.3373756
• Molar Refractivity: 66.6101 cm^3
• Polarizability: 26.771713 Å^3
• Polar Surface Area: 121.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Pink Solid
• Melting Point: >215°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C181200

Ligand used for the preparation of an affinity resin highly specific for glucosidase I purification. Glucosidase I is involved in the post-translational processing of N-linked glycoproteins.

REFERENCES

• HettKamp, H., et al.: Eur. J. Biochem., 142, 85 (1984)
• Shailubhai, K., et al.: Biochem. J., 247, 555 (1984)
• Bause, E., et al.: FEBS, 278, 167 (1991)