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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gc0-2961000000-10e3ffe56d1491c35d8aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gc0-2961000000-10e3ffe56d1491c35d8aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0930000000-725e277ca1152a7fbc98View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-9400000000-615dd94b06b3e5e78526View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0pk9-5359600000-e93f868058ca84374468View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ec8c949182af76945e86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-7a0472476f07853a992bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a70-9300000000-74777b41198e9cd46262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-06ds-9000000000-2d40464867d71e6c1135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01b9-9400000000-d5de17e2c0c42a02efc0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-0435329cc0eb001898faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-1900000000-f47818211aa007edc5f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-c7c9eb2eaa1f91ac9951View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-072c615a4ace0aca930aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-3900000000-5f8e27814cf4a835d41aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar0-6900000000-9a9aef2bcc37f743beabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100000000-4892df7d8d2a53c17d7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9300000000-cd9f8103b846d70baac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-650b3c2ec9303d9b2a96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-232c502ee9a5b93d5a17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fu-1900000000-a9b5237063a8327d87cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-9500000000-aadb547d81673dce1915View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mm-9100000000-0a3f8e5a08a10aa888ebView in MoNA
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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