(2R,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol hydrochloride

• ChemBase ID: 153391
• Molecular Formular: C6H14ClNO4
• Molecular Mass: 199.63266
• Monoisotopic Mass: 199.06113561
• SMILES: C1[C@H]([C@H]([C@H](N1)[C@@H](CO)O)O)O.Cl
• Canonical SMILES: OC[C@H]([C@H]1NC[C@H]([C@H]1O)O)O.Cl
• InChI: InChI=1S/C6H13NO4.ClH/c8-2-4(10)5-6(11)3(9)1-7-5;/h3-11H,1-2H2;1H/t3-,4-,5-,6-;/m1./s1
• InChIKey: IFRNNJQXHHLGKS-MVNLRXSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol hydrochloride
• IUPAC Traditional name: (2R,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol hydrochloride
• Synonyms: (2R,3S,4R)-2-[(1S)-1,2-Dihydroxyethyl]-3,4-pyrrolidinediol Hydrochloride; 1,4-Dideoxy-1,4-imino-D-mannitol, Hydrochloride; 1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride

Database IDs

• CAS Number: 114976-76-0
• MDL Number: MFCD01310868
• PubChem SID: 162247530
• PubChem CID: 11194983

CALCULATED PROPERTIES

• Acid pKa: 13.163428
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -5.9524345
• LogD (pH = 7.4): -4.529607
• Log P: -2.8857431
• Molar Refractivity: 36.5744 cm^3
• Polarizability: 15.1906805 Å^3
• Polar Surface Area: 92.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Needles
• Melting Point: 147-148°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C6H13NO4 · HCl

DETAILS

Toronto Research Chemicals - D439980

A competitive glycosidase inhibitor. It is also a glycoprotein mannosidase inhibitor - inhibiting jack bean, and to a lesser extent lysosomal alpha-mannosidase. It is an azofuranose analog of mannose, and is structurally related to swainsonine.

REFERENCES

• Bashyal, B.P., et al.: Tetrahedron, 43, 3083-3093 (1987)