Survey with prize
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 Date2005-11-16 15:48:42 UTC
Update Date2019-04-01 19:19:17 UTC
HMDB IDHMDB0000625
Secondary Accession Numbers
  • HMDB0003373
  • HMDB00625
  • HMDB03373
Metabolite Identification
Common NameGluconic acid
DescriptionGluconic acid occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. Glucono delta lactone is a cyclic ester of D-gluconic acid. Gluconic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).
Structure
Data?1547234090
Synonyms
ValueSource
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acidChEBI
D-Gluco-hexonic acidChEBI
D-GluconsaeureChEBI
D-GlukonsaeureChEBI
Dextronic acidChEBI
Glycogenic acidChEBI
Hexonic acidChEBI
Maltonic acidChEBI
D-GluconateKegg
(2R,3S,4R,5R)-2,3,4,5,6-PentahydroxyhexanoateGenerator
D-Gluco-hexonateGenerator
DextronateGenerator
GlycogenateGenerator
HexonateGenerator
MaltonateGenerator
D-Gluconic acidGenerator
GluconateGenerator
2,3,4,5,6-Pentahydroxy-hexanoateHMDB
2,3,4,5,6-Pentahydroxy-hexanoic acidHMDB
2,3,4,5,6-PentahydroxyhexanoateHMDB
2,3,4,5,6-Pentahydroxyhexanoic acidHMDB
GCOHMDB
GlosantoHMDB
GlyconateHMDB
Glyconic acidHMDB
PentahydroxycaproateHMDB
Pentahydroxycaproic acidHMDB
Boron gluconateHMDB
Gluconic acid, (113)indium-labeledHMDB
Gluconic acid, calcium saltHMDB
Gluconic acid, cesium(+3) saltHMDB
Gluconic acid, lanthanum(+3) saltHMDB
Gluconic acid, sodium saltHMDB
Gluconic acid, strontium (2:1) saltHMDB
MagnerotHMDB
Manganese gluconateHMDB
Sodium gluconateHMDB
Zinc gluconateHMDB
Gluconic acid, (159)dysprosium-labeled saltHMDB
Gluconic acid, aluminum (3:1) saltHMDB
Gluconic acid, ammonium saltHMDB
Gluconic acid, magnesium (2:1) saltHMDB
Gluconic acid, (14)C-labeledHMDB
Gluconic acid, 1-(14)C-labeledHMDB
Gluconic acid, 6-(14)C-labeledHMDB
Gluconic acid, cobalt (2:1) saltHMDB
Gluconic acid, copper saltHMDB
Gluconic acid, manganese (2:1) saltHMDB
Gluconic acid, potassium saltHMDB
Gluconic acid, tin(+2) saltHMDB
Gluconic acid, zinc saltHMDB
Lithium gluconateHMDB
Magnesium gluconateHMDB
Gluconic acid, (99)technecium (5+) saltHMDB
Gluconic acid, fe(+2) salt, dihydrateHMDB
Gluconic acid, monolithium saltHMDB
Gluconic acid, monopotassium saltHMDB
Gluconic acid, monosodium saltHMDB
Chemical FormulaC6H12O7
Average Molecular Weight196.1553
Monoisotopic Molecular Weight196.058302738
IUPAC Name(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
Traditional Namegluconate
CAS Registry Number526-95-4
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 KeyRGHNJXZEOKUKBD-SQOUGZDYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Gluconic_acid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility316 mg/mL at 25 °CMERCK INDEX (1996)
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility159 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m³·mol⁻¹ChemAxon
Polarizability17.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0932000000-202af87cea2d1f7184abJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-005a-0920000000-2308d9356bc5bb01420eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014j-0950000000-61ab7adf15e353df4ba2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0le9-1964000000-5eb7d6777170e1ad5fa0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0932000000-202af87cea2d1f7184abJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0le9-1964000000-5eb7d6777170e1ad5fa0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0931000000-b07fcc4ac1e6701d32c8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0930000000-181f7b697b591cf8080bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tu-9500000000-ebe398c88f74bb51e702JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-03fr-6121297000-698854fa2453487a1d69JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-06vj-1900000000-78e4a5d92be678c068e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03ds-5900000000-f5d8284baa473ce9d77fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9500000000-7c5b20eef98d0e3d6cbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-b2632ca9154cc5e44438JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-002b-5900000000-4a3066f9dfd6653682fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-50f63dfd017a8380a47cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-91ccf7c8949c1c9d852aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-b2632ca9154cc5e44438JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-5900000000-cf9b480ac397acfebc71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-eca61f6a9c0f1d06e84dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9000000000-91ccf7c8949c1c9d852aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-42150530e3232b66059bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9500000000-763d7b03787732284c19JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9100000000-040569af699927ca6859JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ic-9800000000-3571d4f2ff79bc0d7fa0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-3cb207fadbe1fcae5cb7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-8c900935a94065d0938bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.295 +/- 0.534 uMAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
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
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified45.49 +/- 24.12 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified13.3 (8.2-26.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified35.0+/-29.0 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified21.5 (8.1-38.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified63.463 +/- 28.036 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.732 +/- 0.687 uMAdult (>18 years old)Both
Schizophrenia
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified65.277 +/- 47.794 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB13180
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001980
KNApSAcK IDC00007303
Chemspider ID10240
KEGG Compound IDC00257
BioCyc IDGLUCONATE
BiGG IDNot Available
Wikipedia LinkGluconic_acid
METLIN ID345
PubChem Compound10690
PDB IDNot Available
ChEBI ID33198
References
Synthesis ReferenceAnastassiadis, Savas; Morgunov, Igor G. Gluconic acid production. Recent Patents on Biotechnology (2007), 1(2), 167-180.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  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 ]
  2. Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. [PubMed:3128683 ]

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
Gluconolactone + Water → Gluconic aciddetails
General function:
Involved in shikimate kinase activity
Specific function:
Not Available
Gene Name:
IDNK
Uniprot ID:
Q5T6J7
Molecular weight:
20577.63
Reactions
Adenosine triphosphate + Gluconic acid → ADP + 6-Phosphogluconic aciddetails