N-Acetyl-D-glucosamine (BioCAD00000014507)

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Metabolite Card

Formula: C8H15NO6 (221.0899)
SMILES: CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

Synonyms [en]

N-Acetyl-D-Glucosamine; GlcNAc; 2-Acetamido-2-Deoxy-D-Glucose; N-Acetylchitosamine; 2-Acetamido-2-Deoxy-D-Glucopyranose; N-Acetylglucosamine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

N-Acetyl-D-glucosamine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000014507). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

N-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).

Cytoplasm Membrane Lysosome
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 72-87-7
  • CAS Registry Number: 7512-17-6
  • PubChem: 3440
  • PubChem: 439174
  • ChEBI: ChEBI:17411
  • ChEBI: ChEBI:506227
  • HMDB: HMDB0000215
  • KEGG: C00140
  • BioCyc: N-ACETYL-BETA-D-GLUCOSAMINE
  • BioCyc: N-acetyl-D-glucosamine
  • NCBI MeSH: Acetylglucosamine
  • DrugBank: DB00141
  • RefMet: RM0042984
  • MoNA: CCMSLIB00005720325
  • MoNA: CCMSLIB00005720629
  • MoNA: EMBL-MCF_spec159554
  • MoNA: EMBL-MCF_spec159556
  • MoNA: EMBL-MCF_spec159562
  • MoNA: EMBL-MCF_spec159569
  • MoNA: EMBL_MCF_2_0_HRMS_Library000342
  • MoNA: HMDB0000215_c_ms_99541
  • MoNA: HMDB0000215_c_ms_99542
  • MoNA: HMDB0000215_c_ms_99543
  • MoNA: HMDB0000215_c_ms_99544
  • MoNA: HMDB0000215_c_ms_99545
  • MoNA: HMDB0000215_c_ms_99546
  • MoNA: KZ000248
  • MoNA: MoNA002010
  • MoNA: MoNA002011
  • MoNA: MoNA002012
  • MoNA: MoNA010310
  • MoNA: MoNA010311
  • MoNA: MoNA010312
  • MoNA: MoNA010313
  • MoNA: MoNA010314
  • MoNA: MoNA010315
  • MoNA: MoNA016609
  • MoNA: MoNA016710
  • MoNA: MoNA016875
  • MoNA: MoNA034261
  • MoNA: MoNA034264
  • MoNA: MoNA034266
  • MoNA: MoNA037235
  • MoNA: OUF00363
  • MoNA: OUF00364
  • MoNA: PR010178
  • MoNA: PR010179
  • MoNA: PR010180
  • MoNA: PT103030
  • Metlin: METLIN_3356
  • Coconut NaturalProduct: CNP0246160.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00022 3.2.1.52 chitobiose N-acetylglucosaminohydrolase
KEGG:R01200 3.5.1.33 N-acetyl-D-glucosamine amidohydrolase
KEGG:R01201 2.7.1.59 ATP:N-acetyl-D-glucosamine 6-phosphotransferase
KEGG:R01203 1.1.3.29 N-acetyl-D-glucosamine:oxygen 1-oxidoreductase
KEGG:R01204 2.3.1.3 acetyl-CoA:D-glucosamine N-acetyltransferase
KEGG:R01205 2.4.1.90 UDP-alpha-D-galactose:N-acetyl-D-glucosamine 4-beta-D-galactosyltransferase
KEGG:R01206 3.2.1.14 [1,4-(N-acetyl-beta-D-glucosaminyl)]n glycanohydrolase
KEGG:R01207 5.1.3.8 N-acetyl-D-glucosamine 2-epimerase
KEGG:R01266 3.2.2.11 1-beta-aspartyl-N-acetyl-D-glucosaminylamine L-asparaginohydrolase
KEGG:R04373 3.1.4.45 glycoprotein-N-acetyl-D-glucosaminyl-phospho-D-mannose N-acetyl-D-glucosaminylphosphohydrolase
KEGG:R05199 2.7.1.193 protein-N(pi)-phosphohistidine:N-acetyl-D-glucosamine 6-phosphotransferase
KEGG:R05326 2.4.1.211 beta-D-galactopyranosyl-(13)-N-acetyl-D-hexosamine:phosphate galactosyltransferase
KEGG:R06055 2.4.1.90 UDP-galactose:N-acetyl-D-glucosamine 4-beta-D-galactosyltransferase
KEGG:R06057 2.4.1.211 beta-D-galactopyranosyl-(1->3)-N-acetyl-D-hexosamine:phosphate galactosyltransferase
KEGG:R06081 3.2.1.14 G10483 + C00001<=>C00140 + G10483
KEGG:R06141 3.2.1.52 G10336 + C00001<=>2 C00140
KEGG:R07809 3.2.1.52 G13074 + C00001<=>G01391 + C00140
KEGG:R07816 3.2.1.50 G13038 + C00001<=>G13039 + C00140
KEGG:R08968 2.7.1.162 ATP:N-acetyl-D-glucosamine 1-phosphotransferase
KEGG:R09323 3.2.1.52 G13057 + C00001<=>C00140 + G13058
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY-6517 N-acetylglucosamine degradation II
BioCyc:META_PWY-7581 N-acetylneuraminate and N-acetylmannosamine degradation II
BioCyc:META_PWY-6906 chitin derivatives degradation
BioCyc:ARA_PWY-6902 chitin degradation II (Vibrio)
BioCyc:THAPS_PWY-6902 chitin degradation II
BioCyc:META_PWY-6902 chitin degradation II (Vibrio)
BioCyc:META_PWY-7586 β-1,4-D-mannosyl-N-acetyl-D-glucosamine degradation
BioCyc:AGRO_PWY-6517 N-acetylglucosamine degradation II
BioCyc:BTHE_PWY-6902 chitin degradation II
BioCyc:META_PWY-6517 N-acetylglucosamine degradation II
BioCyc:META_PWY-7822 chitin degradation III (Serratia)
BioCyc:VCHO_PWY-6902 chitin degradation II (Vibrio)
BioCyc:THAPS_PWY-6906 chitin derivatives degradation
BioCyc:PDIF272563_PWY-6517 N-acetylglucosamine degradation II
BioCyc:LACTORHA_PWY-6902 chitin degradation II
BioCyc:META_PWY-6855 chitin degradation I (archaea)
BioCyc:META_PWY-7645 hyaluronan degradation
BioCyc:MTBH37RV_PWY-6902 chitin degradation II (Vibrio)
BioCyc:ANTHRA_PWY-6902 chitin degradation II
BioCyc:PDIF272563_PWY-6902 chitin degradation II (Vibrio)
View All Pathways