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

• ChemBase ID: 91936
• Molecular Formular: C12H23NO6
• Molecular Mass: 277.31412
• Monoisotopic Mass: 277.15253746
• SMILES: OC[C@@H]1[C@@H](O)[C@H](O)[C@H](O)CN1CCCCCC(=O)O
• Canonical SMILES: OC[C@H]1N(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-CNVPUSNMSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 104154-10-1
• MDL Number: MFCD01320382
• PubChem SID: 162078634
• PubChem CID: 49759910

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: Hot Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 160-165°C; 162-165°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Apollo Scientific Ltd - OR8115T

Ligand used for the preparation of an affinity resin specific for Mang mannosidase, an enzyme involved in the post-translational processing of N-linked glycoprotein.

Toronto Research Chemicals - C181150

Ligand used for the preparation of an affinity resin specific for Man9 mannosidase, an enzyme involved in the post-translational processing of N-linked glycoprotein (Man)9(GlcNAc)2.

REFERENCES

• Schweden, J., et al.: Eur. J. Biochem., 157, 563 (1986)