N-Acetyl-D-Glucosamine

Details

• Internal ID: 4a66a55f-1281-4547-8329-6ffd6956cf3c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Amino sugars > Acylaminosugars
• IUPAC Name: N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• SMILES (Canonical): CC(=O)NC1C(C(C(OC1O)CO)O)O
• SMILES (Isomeric): CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](OC1O)CO)O)O
• 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
• InChI Key: OVRNDRQMDRJTHS-RTRLPJTCSA-N
• Popularity: 20,506 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 221.21 g/mol
• Exact Mass: 221.08993720 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: -1.70

Synonyms

• 2-Acetamido-2-Deoxy-D-Glucopyranoside
• 2-Acetamido-2-Deoxy-D-Glucose
• 2-Acetamido-2-Deoxy-Glucopyranose
• 2-Acetamido-2-Deoxy-Glucopyranoside
• 2-Acetamido-2-Deoxy-Glucose
• 2-Deoxy-2-Acetamido-D-Glucopyranose
• 2-Deoxy-2-Acetamido-D-Glucopyranoside
• 2-Deoxy-2-Acetamido-D-Glucose
• 2-Deoxy-2-Acetamido-Glucopyranose
• 2-Deoxy-2-Acetamido-Glucopyranoside
• 2-Deoxy-2-Acetamido-Glucose
• D-GlcNAc
• GlcNAc
• N-Acetyl-D-Glucosamine
• N-Acetyl-Glucosamine
• N-Acetylchitosamine
• acetylglucosamine
• CHEBI:506227
• N-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
• N-Acetyl-D-glucosamine-Agarose
• NAcGlc
• N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• N-Acetyl-2-amino-2-deoxy-D-glucose
• 72-87-7
• N-Acetyl Glucosamine
• SMR000857242
• 2-(Acetylamino)-2-deoxyhexopyranose #
• Epitope ID:137340
• MLS001333127
• MLS001333128
• SCHEMBL468802
• 2-(Acetylamino)-2-deoxyhexose
• CHEMBL240524
• n-acetyl-2-amino-2-deoxyglucose
• N-Acetylglucosamine cyclized form
• DTXCID30820152
• DTXSID901045903
• HMS2230N05
• N-Acetyl-D-glucosamine, >=99%
• 2-acetamido-2-deoxy-d-glu-copyranose
• 2-Acetamido-2-deoxy -D-glucopyranose
• AKOS015914726
• N-Acetyl-D-glucosamine, >=95% (HPLC)
• A0092
• CS-0326546
• C00140
• A838328
• A887912
• EN300-19632131
• N-acetyl-D-glucosamine (incomplete stereochemistry)
• Q27225758
• N_FULL/O_FULL_01000000000000_GS_1219
• N-Acetyl-D-glucosamine, suitable for cell culture, BioReagent
• WURCS=2.0/1,1,0/(a2122h-1x_1-5_2*NCC/3=O)/1/
• N-Acetylglucosamine, United States Pharmacopeia (USP) Reference Standard
• N-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)acetamide
• N-Acetylglucosamine, Pharmaceutical Secondary Standard; Certified Reference Material

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	562.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.35%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.04%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	87.81%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.83%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.43%	94.33%
CHEMBL2581	P07339	Cathepsin D	84.03%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	83.09%	95.93%
CHEMBL4040	P28482	MAP kinase ERK2	82.33%	83.82%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.46%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.95%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.26%	85.14%

Plants that contains it

• Prunus persica

Cross-Links

• PubChem: 439174
• LOTUS: LTS0075677
• wikiData: Q27225758