You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 21:33:03 UTC
Update Date2017-12-07 01:52:18 UTC
HMDB IDHMDB0003466
Secondary Accession Numbers
  • HMDB03466
Metabolite Identification
Common NameL-Gulonolactone
DescriptionL-Gulonolactone (also known as reduced ascorbic acid, RAA) is the substrate of the enzyme L-gulono-1,4-lactone oxidoreductase (EC 1.1.3.8), which catalyzes the last step of the biosynthesis of L-ascorbic acid (vitamin C) in plants and animals. The enzyme L-Gulono-1,4-lactone oxidase is missing in scurvy-prone, vitamin C-deficient animals, such as humans. L-Gulonolactone is present in human blood and has been used as one of the markers to compare changes in exercise-induced oxidative stress. (PMID: 16956367 , 16494601 ).
Structure
Thumb
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
GulonolactoneMeSH
Gulonolactone, (D)-isomerMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as gamma butyrolactones. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassLactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Oxolane
  • 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
Physiological effect

Health effect:

  Health condition:

    Cancer:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

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
Water Solubility637 g/LALOGPS
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
Polarizability15.56 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023179
KNApSAcK IDNot Available
Chemspider ID388493
KEGG Compound IDC01040
BioCyc ID2-KETO-L-GULONOLACTONE
BiGG ID36677
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439373
PDB IDNot Available
ChEBI ID17587
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wolucka BA, Communi D: Mycobacterium tuberculosis possesses a functional enzyme for the synthesis of vitamin C, L-gulono-1,4-lactone dehydrogenase. FEBS J. 2006 Oct;273(19):4435-45. Epub 2006 Sep 5. [PubMed:16956367 ]
  2. Steinberg JG, Delliaux S, Jammes Y: Reliability of different blood indices to explore the oxidative stress in response to maximal cycling and static exercises. Clin Physiol Funct Imaging. 2006 Mar;26(2):106-12. [PubMed:16494601 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:
RGN
Uniprot ID:
Q15493
Molecular weight:
33252.53
Reactions
L-Gulonolactone + Water → Gulonic aciddetails