(3R,4R,5S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol

• ChemBase ID: 127571
• Molecular Formular: C6H13NO5
• Molecular Mass: 179.17112
• Monoisotopic Mass: 179.07937252
• SMILES: N[C@H]1C(O)OC(CO)[C@@H](O)[C@@H]1O
• Canonical SMILES: OCC1OC(O)[C@@H]([C@H]([C@@H]1O)O)N
• InChI: InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2?,3-,4-,5-,6?/m1/s1
• InChIKey: MSWZFWKMSRAUBD-SPZCMYQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,5S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
• IUPAC Traditional name: glucosamine
• Synonyms: 2-Amino-2-deoxy-glucose; Chitosamine; Glucosamine

Database IDs

• CAS Number: 3416-24-8
• EC Number: 222-311-2
• Beilstein Number: 1723616
• PubChem SID: 162221890
• PubChem CID: 439213; 121837
• CHEBI ID: 5417
• ATC CODE: M01AX05
• CHEMBL: 181132
• Chemspider ID: 388352
• DrugBank ID: DB01296
• Gmelin ID: 720725
• KEGG ID: D04334
• MeSH Name: Glucosamine
• Unique Ingredient Identifier: N08U5BOQ1K
• Wikipedia Title: Glucosamine

CALCULATED PROPERTIES

• Acid pKa: 11.726975
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.5965767
• LogD (pH = 7.4): -3.9292529
• Log P: -3.039421
• Molar Refractivity: 37.5809 cm^3
• Polarizability: 15.959335 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 150°C
• Density: 1.563 g/mL
• Partition Coefficient: -2.175
• pKa: 12.273
• pKb: 1.724