Common NameN-acetyl-d-glucosamine
DescriptionN-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. (PMID 16237703 ).
Structure
Molecular FormulaC8H15NO6
Average Mass221.20780
Monoisotopic Mass221.08994
IUPAC NameN-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameGlcnac
CAS Registry Number7512-17-6
SMILESCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=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
InChI KeyOVRNDRQMDRJTHS-RTRLPJTCSA-N
CHEBI IDCHEBI:506227
HMDB IDHMDB0000215
Pathways
NameSMPDB/PathBank
Amino Sugar Metabolism
Sialuria or French Type Sialuria
Salla Disease/Infantile Sialic Acid Storage Disease
Tay-Sachs Disease
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
StateSolid
Water Solubility2.54e+02 g/l
logP-2.60
logS0.06
pKa (Strongest Acidic)11.60
pKa (Strongest Basic)-0.78
Hydrogen Acceptor Count6
Hydrogen Donor Count5
Polar Surface Area119.25 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity47.02 m³·mol⁻¹
Polarizability20.56

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