CHEBI:16217 - D-glucono-1,5-lactone

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ChEBI Name D-glucono-1,5-lactone
ChEBI ID CHEBI:16217
ChEBI ASCII Name D-glucono-1,5-lactone
Definition An aldono-1,5-lactone obtained from D-gluconic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43753, CHEBI:12957, CHEBI:20988, CHEBI:4159
Supplier Information ChemicalBook:CB1494336, eMolecules:514568, ZINC000002539702
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Wikipedia License
Glucono-δ-lactone (GDL), also known as gluconolactone, is an organic compound with the formula (HOCH)3(HOCH2CH)CO2. A colorless solid, it is an oxidized derivative of glucose. It is typically produced by the aerobic oxidation of glucose in the presence of the enzyme glucose oxidase. The conversion cogenerates hydrogen peroxide, which is often the key product of the enzyme: C6H12O6 + O2 → C6H10O6 + H2O2 Gluconolactone spontaneously hydrolyzes to gluconic acid: C6H10O6 + H2O → C6H12O7
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Formula C6H10O6
Net Charge 0
Average Mass 178.14000
Monoisotopic Mass 178.04774
InChI InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
InChIKey PHOQVHQSTUBQQK-SQOUGZDYSA-N
SMILES OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Tetranychus urticae (NCBI:txid32264) See: PubMed
Roles Classification
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
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ChEBI Ontology
Outgoing D-glucono-1,5-lactone (CHEBI:16217) has functional parent D-gluconic acid (CHEBI:33198)
D-glucono-1,5-lactone (CHEBI:16217) has role animal metabolite (CHEBI:75767)
D-glucono-1,5-lactone (CHEBI:16217) has role mouse metabolite (CHEBI:75771)
D-glucono-1,5-lactone (CHEBI:16217) is a aldono-1,5-lactone (CHEBI:74105)
D-glucono-1,5-lactone (CHEBI:16217) is a gluconolactone (CHEBI:24267)
Incoming 6-O-phosphono-D-glucono-1,5-lactone (CHEBI:16938) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
6-O-sinapoyl-D-glucono-1,5-lactone (CHEBI:60076) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
6-deoxy-6-sulfoglucono-1,5-lactone (CHEBI:88250) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-cellohexaono-1,5-lactone (CHEBI:143174) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-cellopentaono-1,5-lactone (CHEBI:143173) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-cellotriono-1,5-lactone (CHEBI:143171) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-maltobiono-1,5-lactone (CHEBI:143029) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-maltoheptaono-1,5-lactone (CHEBI:143188) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-maltohexaono-1,5-lactone (CHEBI:143187) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-maltopentaono-1,5-lactone (CHEBI:143186) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-maltotetraono-1,5-lactone (CHEBI:143185) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-maltotriono-1,5-lactone (CHEBI:143184) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
cellobiono-1,5-lactone (CHEBI:17863) has functional parent D-glucono-1,5-lactone (CHEBI:16217)
D-cellotetraono-1,5-lactone (CHEBI:143172) is a D-glucono-1,5-lactone (CHEBI:16217)
lactobiono-1,5-lactone (CHEBI:143068) is a D-glucono-1,5-lactone (CHEBI:16217)
IUPAC Name
(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Synonyms Sources
(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one IUPAC
1,5-D-gluconolactone ChemIDplus
1,5-Gluconolactone KEGG COMPOUND
D-Aldonolactone KEGG COMPOUND
D-gluconic acid δ-lactone ChemIDplus
D-gluconic acid lactone ChemIDplus
D-Glucono-1,5-lactone KEGG COMPOUND
D-glucono-1,5-lactone UniProt
D-Gluconolactone KEGG COMPOUND
D-threo-Aldono-1,5-lactone KEGG COMPOUND
δ-D-gluconolactone ChemIDplus
delta-Gluconolactone KEGG COMPOUND
Glucarolactone KEGG COMPOUND
Gluconic acid lactone KEGG COMPOUND
gluconic δ-lactone ChemIDplus
Gluconic lactone KEGG COMPOUND
Gluconolactone KEGG COMPOUND
Gluconolactone ChemIDplus
Manual Xrefs Databases
5144 DrugCentral
C00198 KEGG COMPOUND
D04332 KEGG DRUG
DB04564 DrugBank
Gluconolactone Wikipedia
HMDB0000150 HMDB
LGC PDBeChem
View more database links
Registry Numbers Types Sources
50890 Gmelin Registry Number Gmelin
83286 Reaxys Registry Number Reaxys
90-80-2 CAS Registry Number KEGG COMPOUND
90-80-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23349779 PubMed citation Europe PMC
24392858 PubMed citation Europe PMC
Last Modified
22 February 2017