Showing metabocard for L-Gulonolactone (BMDB0003466)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:04:51 UTC
Update Date2020-05-05 18:38:09 UTC
BMDB IDBMDB0003466
Secondary Accession Numbers
  • BMDB03466
Metabolite Identification
Common NameL-Gulonolactone
DescriptionL-Gulonolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. L-Gulonolactone exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on L-Gulonolactone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
gamma-GulonolactoneChEBI
L-Gulonic acid gamma-lactoneChEBI
L-Gulono-gamma-lactoneChEBI
g-GulonolactoneGenerator
Γ-gulonolactoneGenerator
L-Gulonate g-lactoneGenerator
L-Gulonate gamma-lactoneGenerator
L-Gulonate γ-lactoneGenerator
L-Gulonic acid g-lactoneGenerator
L-Gulonic acid γ-lactoneGenerator
L-Gulono-g-lactoneGenerator
L-Gulono-γ-lactoneGenerator
L-(+)-gulono-1,4-LactoneHMDB
L-Gulono-1,4-lactoneHMDB
Reduced ascorbateHMDB
Reduced ascorbic acidHMDB
Gulonolactone, (L)-isomerMeSH, HMDB
GulonolactoneMeSH, HMDB
Gulonolactone, (D)-isomerMeSH, HMDB
Dihydroascorbic acidHMDB
L-(+)-Gulonic acid gamma-lactoneHMDB
L-(+)-Gulonic acid γ-lactoneHMDB
L-GulonolactoneHMDB
Chemical FormulaC6H10O6
Average Molecular Weight178.14
Monoisotopic Molecular Weight178.047738052
IUPAC Name(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
Traditional NameL-gulonolactone
CAS Registry Number1128-23-0
SMILES
[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1
InChI KeySXZYCXMUPBBULW-SKNVOMKLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.571Not Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.7ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability15.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003466
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023179
KNApSAcK IDC00053429
Chemspider ID388493
KEGG Compound IDC01040
BioCyc IDL-GULONO-1-4-LACTONE
BiGG ID36677
Wikipedia LinkL-gulonolactone oxidase
METLIN IDNot Available
PubChem Compound439373
PDB IDNot Available
ChEBI ID17587
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. L-gulonolactone oxidase
General function:
Energy production and conversion
Specific function:
Oxidizes L-gulono-1,4-lactone to hydrogen peroxide and L-xylo-hexulonolactone which spontaneously isomerizes to L-ascorbate.
Gene Name:
GULO
Uniprot ID:
Q3ZC33
Molecular weight:
50282.0