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

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ChEBI Name	N-acetyl-D-glucosamino-1,5-lactone

ChEBI ID	CHEBI:42870

ChEBI ASCII Name	N-acetyl-D-glucosamino-1,5-lactone

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C8H13NO6

Net Charge

Average Mass

219.193

Monoisotopic Mass

219.07429

InChI

InChI=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

InChIKey

NELQYZRSPDCGRQ-DBRKOABJSA-N

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1=O

Metabolite of Species	Details
Telmessus cheiragonus (NCBI:txid324081)	Found in urine (BTO:0001419). See: PubMed
Callinectes sapidus (NCBI:txid6763)	Found in urine (BTO:0001419). See: PubMed

Roles Classification
Biological Role(s):	pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. EC 2.3.2.52 (beta-N-acetylhexosaminidase) inhibitor An EC 2.3.2.* (aminoacyltransferase) inhibitor that interferes with the action of beta-N-acetylhexosaminidase (EC 2.3.2.52). animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

ChEBI Ontology
Outgoing	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 2.3.2.52 (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	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	Sources
2-(acetylamino)-2-deoxy-D-gluconic acid δ-lactone	ChEBI
2-acetamido-2-deoxy-1,5-gluconolactone	ChemIDplus
2-acetamido-2-deoxy-D-glucono-(1,5)-lactone	ChemIDplus
2-acetamido-2-deoxy-D-glucono-(1→5)-lactone	ChEBI
2-acetamido-2-deoxy-D-glucono-1,5-lactone	DrugBank
2-acetamido-2-deoxy-D-glucono-δ-lactone	ChEBI
2-acetamido-2-deoxy-D-gluconolactone	ChEBI
CD 80110	ChemIDplus
CD-80110	ChemIDplus
N-acetyl-D-glucosamino-1,5-lactone	UniProt
N-acetylglucosamino-1,5-lactone	ChEBI

Last Modified

18 May 2023