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

• ChemBase ID: 27
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: [C@H]1([C@H]([C@@H]([C@H](OC1O)CO)O)O)NC(=O)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-RTRLPJTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-acetyl-D-glucosamine
• Brand Name: Aflexa; Natures Blend Glucosamine; GS-500; Maxi GS
• Synonyms: 2-Acetamido-2-deoxy-D-glucose; GlcNAc; Glucosamine Complex; N-Acetylchitosamine; NAG; N-Acetyl-D-glucosamine

Database IDs

• CAS Number: 7512-17-6
• PubChem SID: 160963490
• PubChem CID: 439174

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.6
• LOG S: 0.06
• Solubility (Water): 2.54e+02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.1

DETAILS

DrugBank - DB00141

• Drug Groups: approved; nutraceutical
• Description: The N-acetyl derivative of glucosamine. [PubChem]
• Indication: For the treatment and prevention of osteoarthritis, by itself or in combination with chondroitin sulfate.
• Toxicity: Mouse, intravenous LD₅₀ is 4170 mg/kg. Side effects that have been reported are mainly mild gastrointestinal complaints such as heartburn, epigastric distress and diarrhea. No allergic reactions have been reported including sulfa-allergic reactions to glucosamine sulfate.
• Affected Organisms: Humans and other mammals
• Biotransformation: A significant fraction of ingested glucosamine is catabolized by first-pass metabolism in the liver.
• Absorption: Approximately 90% of orally administered glucosamine (salt form) gets absorbed from the small intestine.
• External Links: PDRhealth