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

• ChemBase ID: 109276
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: O=C(N[C@H]1[C@@H](O)[C@H](O)[C@H](OC1O)CO)C
• Canonical SMILES: OC[C@H]1OC(O)[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8?/m1/s1
• InChIKey: OVRNDRQMDRJTHS-ZTVVOAFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: ManNAc
• Synonyms: N-ACETYL-D-MANNOSAMINE; 2-(Acetylamino)-2-deoxy-D-mannopyranose; N-Acetylmannosamine; N-Acetyl-D-mannosamine-6-3H

Database IDs

• CAS Number: 7772-94-3; 3615-17-6
• PubChem SID: 162094930
• PubChem CID: 439281

CALCULATED PROPERTIES

• Acid pKa: 11.60413
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2205749
• LogD (pH = 7.4): -3.2206008
• Log P: -3.2205744
• Molar Refractivity: 47.0247 cm^3
• Polarizability: 19.398714 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Sp. Act. ~35 mCi/mmol.; White to Off-White Solid
• Melting Point: 126-130°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

MP Biomedicals - 05210431

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - A186199

A derivative of D-Mannosamine (M167000).

REFERENCES

• Pukanud, P. et al.: Drug Delivery, 16, 289 (2009)