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Record Information
Version3.6
Creation Date2006-05-22 15:12:47 UTC
Update Date2016-05-13 21:11:46 UTC
HMDB IDHMDB03290
Secondary Accession NumbersNone
Metabolite Identification
Common NameGulonic acid
DescriptionReduction product of glucuronic acid; oxidation product of l-gulose.
Structure
Thumb
Synonyms
ValueSource
D-GulonateHMDB
D-Gulonic acidHMDB
GulonateHMDB
L-GulonateHMDB
L-Gulonic acidHMDB
Chemical FormulaC6H12O7
Average Molecular Weight196.1553
Monoisotopic Molecular Weight196.058302738
IUPAC Name(2R,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
Traditional Namegulonic acid
CAS Registry Number20246-53-1
SMILES
OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5-/m1/s1
InChI KeyInChIKey=RGHNJXZEOKUKBD-KKQCNMDGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Monosaccharide
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility159.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m3·mol-1ChemAxon
Polarizability17.16 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-067l-0897000000-a5adc23ee8062f1b4496View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-51cc4bff4f073ec29dc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-06yk-9200000000-36fd28057c23b3aeb698View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01t9-9200000000-14a6bd042df22e1334ecView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023136
KNApSAcK IDNot Available
Chemspider ID134243
KEGG Compound IDC00800
BioCyc IDCPD-16836
BiGG ID36035
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03290
Metagene LinkHMDB03290
METLIN ID344
PubChem Compound152304
PDB IDNot Available
ChEBI ID16154
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. ASHWELL G, KANFER J, SMILEY JD, BURNS JJ: Metabolism of ascorbic acid and related uronic acids, aldonic acids, and pentoses. Ann N Y Acad Sci. 1961 Apr 21;92:105-14. [13684759 ]

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
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
CRYL1
Uniprot ID:
Q9Y2S2
Molecular weight:
35418.91
Reactions
Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADHdetails
Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADH + Hydrogen Iondetails