Compound: N-Acetyl-beta-D-glucosamine
SMILES: O=C(N[C@H]1[C@@H](O[C@H](CO)[C@H]([C@@H]1O)O)O)C
InChIKey: OVRNDRQMDRJTHS-FMDGEEDCSA-N
Synonyms: N-Acetyl-beta-D-glucosamine, 2-acetamido-2-deoxy-beta-D-glucopyranose, CHEBI:28009, beta-N-Acetylglucosamin, 2-Acetamido-2-deoxy-beta-D-glucose, 8P59336F68, Glucopyranose, 2-acetamido-2-deoxy-, beta-D-, RefChem:7894, GlyTouCan:G49108TO, G49108TO, Beta-N-Acetylglucosamine, 14131-68-1, N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide, 72-87-7, 103094-10-6, N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide, C8H15NO6, NAcGlc, Cheon shim bo yun, n-acetyl-b-d-glucosamine, 2-acetamido-2-deoxyhexopyranose, betaGlcNAc, GlcNAc-beta, pharmaceutical aid, MFCD00797589, b-N-Acetylglucosamine, Spectrum_000999, Spectrum2_001353, Spectrum3_001400, Spectrum4_001179, b-N-Acetyl-D-glucosamine, bmse000231, Epitope ID:135813, beta-N-Acetyl-D-glucosamine, SCHEMBL19345, BSPBio_003020, KBioGR_001817, KBioSS_001479, 137630-09-2, DivK1c_000352, SPECTRUM1500715, n-acetyl-.beta.-d-glucosamine, SPBio_001565, CHEMBL447878, beta-N-Acetyl-delta-glucosamine, SCHEMBL11283044, HMS501B14, KBio1_000352, KBio2_001479, KBio2_004047, KBio2_006615, KBio3_002240, .BETA.-N-ACETYLGLUCOSAMIN, [4)-beta-D-GlcpNAc(1->]n, 2-Acetamido-2-deoxy-b-D-glucose, NINDS_000352, DTXSID301045979, HMS1921E22, UNII-8P59336F68, N-Acetyl-D-glucosamine, USP grade, BDBM50481442, CCG-39291, EBC-48099, AKOS015960418, AT21015, 2-Acetamido-2-deoxy-beta-delta-glucose, IDI1_000352, NCGC00178341-01, 2-deoxy-2-acetamido-beta-D-glucopyranose, AC-11093, 2-(acetylamino)-2-deoxy-beta-D-glucopyranose, 2-ACETAMIDO-2-DEOXY-.BETA.-D-GLUCOSE, C03878, N-acetyl-D-glucosamine (complete stereochemistry), Q284367, 2-ACETAMIDO-2-DEOXY-.BETA.-D-GLUCOPYRANOSE, GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-, .BETA.-D-, Poly-(b1-4)-N-acetyl glucosamine/Poly-(a1-4)-N-acetyl glucosamine
Theoretical properties:
molecular_formula: C8H15NO6
molecular_weight: 221.21 g/mol
exact_mass: 221.08993720 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 15
topological_polar_surface_area: 119 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Chitin is an aminoglycan consisting of beta-(14)-linked N-acetyl-D-glucosamine residues. It has a role as a vulnerary, a mouse metabolite, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a N-acylglucosamine and an aminoglycan.
chebi: An aminoglycan consisting of β-(1→4)-linked <em>N</em>-acetyl-<small>D</small>-glucosamine residues.
chembl: N-ACETYLGLUCOSAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: N-Acetylglucosamine (GlcNAc) is an amide derivative of the monosaccharide glucose.  It is a secondary amide between glucosamine and acetic acid. It is significant in several biological systems.
It is part of a biopolymer in the bacterial cell wall, which is built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan (formerly called murein).
GlcNAc is the monomeric unit of the polymer chitin, which forms the exoskeletons of arthropods like insects and crustaceans. It is the main component of the radulas of mollusks, the beaks of cephalopods, and a major component of the cell walls of most fungi.
Polymerized with glucuronic acid, it forms hyaluronan.
GlcNAc has been reported to be an inhibitor of elastase release from human polymorphonuclear leukocytes (range 8–17% inhibition), however this is much weaker than the inhibition seen with N-acetylgalactosamine (range 92–100%).