Record Information
Version1.0
Creation date2011-09-21 00:25:49 UTC
Update date2015-07-21 06:57:34 UTC
Primary IDFDB023179
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number1128-23-0
Structure
Thumb
Synonyms
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
Polarizability15.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O6
IUPAC name(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO
Average Molecular Weight178.14
Monoisotopic Molecular Weight178.047738052
Classification
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
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Gulonolactone, 4 TMS, GC-MS Spectrumsplash10-0gc0-2961000000-10e3ffe56d1491c35d8aSpectrum
GC-MSL-Gulonolactone, non-derivatized, GC-MS Spectrumsplash10-0gc0-2961000000-10e3ffe56d1491c35d8aSpectrum
GC-MSL-Gulonolactone, non-derivatized, GC-MS Spectrumsplash10-0fr2-0930000000-725e277ca1152a7fbc98Spectrum
Predicted GC-MSL-Gulonolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08fr-9400000000-615dd94b06b3e5e78526Spectrum
Predicted GC-MSL-Gulonolactone, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pk9-5359600000-e93f868058ca84374468Spectrum
Predicted GC-MSL-Gulonolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ec8c949182af76945e862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-7a0472476f07853a992b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a70-9300000000-74777b41198e9cd462622021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-06ds-9000000000-2d40464867d71e6c11352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01b9-9400000000-d5de17e2c0c42a02efc02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-0435329cc0eb001898fa2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-1900000000-f47818211aa007edc5f42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-c7c9eb2eaa1f91ac99512016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-072c615a4ace0aca930a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-3900000000-5f8e27814cf4a835d41a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar0-6900000000-9a9aef2bcc37f743beab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100000000-4892df7d8d2a53c17d7f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9300000000-cd9f8103b846d70baac02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-650b3c2ec9303d9b2a962021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-232c502ee9a5b93d5a172021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fu-1900000000-a9b5237063a8327d87cd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-9500000000-aadb547d81673dce19152021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mm-9100000000-0a3f8e5a08a10aa888eb2021-09-24View Spectrum
NMRNot Available
ChemSpider ID388493
ChEMBL IDNot Available
KEGG Compound IDC01040
Pubchem Compound ID439373
Pubchem Substance IDNot Available
ChEBI ID17587
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03466
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36677
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference