N-[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-oxooxan-3-yl]acetamide

• ChemBase ID: 2526
• Molecular Formular: C8H13NO6
• Molecular Mass: 219.19192
• Monoisotopic Mass: 219.07428714
• SMILES: CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1=O
• Canonical SMILES: OC[C@H]1OC(=O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H13NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-7,10,12-13H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-/m1/s1
• InChIKey: NELQYZRSPDCGRQ-DBRKOABJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-oxooxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-oxooxan-3-yl]acetamide
• Synonyms: 2-Acetamido-2-Deoxy-D-Glucono-1,5-Lactone; N-Acetylglucosamino-1,5-lactone; 2-Acetamido-2-deoxy-D-gluconolactone

Database IDs

• CAS Number: 19026-22-3
• PubChem SID: 160965976; 46505263
• PubChem CID: 87901

CALCULATED PROPERTIES

JChem

• Molar Refractivity: 45.8801 cm^3
• Polarizability: 18.871698 Å^3
• Polar Surface Area: 116.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 11.598224
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.0333087
• LogD (pH = 7.4): -3.0333328
• Log P: -3.0333083

ALOGPS 2.1

• Solubility (Water): 2.33e+02 g/l
• Log P: -2.04
• LOG S: 0.03

PROPERTIES

Physical Property

• Apperance: White to Off-White Solid
• Melting Point: 168-170°C

Safety Information

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

DETAILS

DrugBank - DB02813

Drug information: experimental

Toronto Research Chemicals - A156000

Used to inhibit breakdown of products by beta-hexosaminidase(s) when the culture medium is used as an enzyme source.

REFERENCES

• Sasaki, K., et al.: Proc. Natl. Acad. Sci. USA, 94, 14294 (1997)