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CHEBI:42870 - N-acetyl-D-glucosamino-1,5-lactone

ChEBI IDCHEBI:42870
ChEBI NameN-acetyl-D-glucosamino-1,5-lactone
Stars
ASCII NameN-acetyl-D-glucosamino-1,5-lactone
DefinitionA deoxygluconolactone that results from the cyclisation and formal condensation of the carboxy group of 2-amino-2-deoxy-D-gluconic acid with its 5-hydroxy group. It is a sex pheromone found in the urine of female blue crabs, Callinectes sapidus.
Last Modified18 May 2023
DownloadsMolfile
FormulaC8H13NO6
Net Charge0
Average Mass219.193
Monoisotopic Mass219.07429
SMILESCC(=O)N[C@H]1C(=O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChIInChI=1S/C8H13NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-7,10,12-13H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-/m1/s1
InChIKeyNELQYZRSPDCGRQ-DBRKOABJSA-N
Species of MetaboliteComponentSourceComments
Callinectes sapidus (ncbitaxon:6763) urine (BTO:0001419) PubMed (28686351)
Telmessus cheiragonus (ncbitaxon:324081) urine (BTO:0001419) PubMed (27132136)
Roles Classification
Biological Roles:
EC 3.2.1.52 (beta-N-acetylhexosaminidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of β-N-acetylhexosaminidase (EC 3.2.1.52).
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
ChEBI Ontology
Outgoing Relation(s)
N-acetyl-D-glucosamino-1,5-lactone (CHEBI:42870) has functional parent 2-amino-2-deoxy-D-gluconic acid (CHEBI:17784)
N-acetyl-D-glucosamino-1,5-lactone (CHEBI:42870) has role animal metabolite (CHEBI:75767)
N-acetyl-D-glucosamino-1,5-lactone (CHEBI:42870) has role EC 3.2.1.52 (β-N-acetylhexosaminidase) inhibitor (CHEBI:184301)
N-acetyl-D-glucosamino-1,5-lactone (CHEBI:42870) has role pheromone (CHEBI:26013)
N-acetyl-D-glucosamino-1,5-lactone (CHEBI:42870) is a deoxygluconolactone (CHEBI:57246)
Incoming Relation(s)
N,N'-diacetylchitobiono-1,5-lactone (CHEBI:143145) has functional parent N-acetyl-D-glucosamino-1,5-lactone (CHEBI:42870)
IUPAC Name 
N-[(3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-oxotetrahydro-2H-pyran-3-yl]acetamide
Synonyms  Source
2-acetamido-2-deoxy-D-glucono-1,5-lactoneDrugBank
CD 80110ChemIDplus
CD-80110ChemIDplus
N-acetylglucosamino-1,5-lactoneChEBI
2-acetamido-2-deoxy-D-glucono-δ-lactoneChEBI
2-(acetylamino)-2-deoxy-D-gluconic acid δ-lactoneChEBI
UniProt Name  Source
N-acetyl-D-glucosamino-1,5-lactoneUniProt
Manual XrefsDatabases
GDLPDBeChem
DB02813DrugBank
79304ChemSpider
Registry NumbersSources
Reaxys:1685090Reaxys
CAS:19026-22-3ChemIDplus
Citations