(2S,3S)-2,3-dihydroxybutanedioic acid; (3R,4R,5R)-5-(hydroxymethyl)piperidine-3,4-diol

• ChemBase ID: 171790
• Molecular Formular: C10H19NO9
• Molecular Mass: 297.25916
• Monoisotopic Mass: 297.10598119
• SMILES: C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.[C@@H]([C@H](O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)O)O.OC[C@H]1CNC[C@H]([C@@H]1O)O
• InChI: InChI=1S/C6H13NO3.C4H6O6/c8-3-4-1-7-2-5(9)6(4)10;5-1(3(7)8)2(6)4(9)10/h4-10H,1-3H2;1-2,5-6H,(H,7,8)(H,9,10)/t4-,5-,6-;1-,2-/m10/s1
• InChIKey: ULBPPCHRAVUQMC-AWUBODBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-dihydroxybutanedioic acid; (3R,4R,5R)-5-(hydroxymethyl)piperidine-3,4-diol
• IUPAC Traditional name: (3R,4R,5R)-5-(hydroxymethyl)piperidine-3,4-diol; D-tartaric acid
• Synonyms: (3R,4R,5R)-5-(Hydroxymethyl)-3,4-piperidinediol (2S,3S)-2,3-Dihydroxybutanedioate; Isofagomine D-Tartrate

Database IDs

• CAS Number: 957230-65-8
• PubChem SID: 164227700
• PubChem CID: 56841032

CALCULATED PROPERTIES

• Acid pKa: 13.516852
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -5.228414
• LogD (pH = 7.4): -3.667671
• Log P: -2.2613895
• Molar Refractivity: 35.4991 cm^3
• Polarizability: 14.5027485 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 146-148°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I816010

Used as human acid β-glucosidase inhibitor and for the treatment of Gaucher disease.

REFERENCES

• Zhou, Z., et al.: J. Biol. Chem., 274, 31123 (1999)
• Pandey, G., et al.: Tetrahedron lett., 41, 8821, (2000).