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Showing Compound D-Gluconic acid (FDB001980)

Record Information
Version1.0
Creation date2010-04-08 22:05:11 UTC
Update date2020-09-17 15:42:27 UTC
Primary IDFDB001980
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Gluconic acid
DescriptionGluconic acid, also known as dextronic acid, 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. Gluconic acid is an extremely weak acid (based on its pKa). Gluconic acid exists in all living species, ranging from bacteria to humans. Gluconic acid is produced in particularly high abundance by certain fungi, such as Aspergillus niger (PMID: 24039465). Gluconic acid occurs naturally in fruit, honey, kombucha tea, and cow’s milk. Gluconic acid and its lactone have also been found in some table wines. The source of gluconic acid is most likely mold metabolism. Industrially, gluconate is used as a concrete admixture (retarder) to slow down the cement hydration reactions and to delay the cement setting time. It is also used in cleaning products where it helps cleaning up mineral deposits. In this regard, gluconic acid has been found to chelate the anions of calcium, iron, aluminium, copper, various rare earths and other heavy metals. The salts of gluconic acid are known as "gluconates". Gluconic acid is also used to maintain the cation-anion balance on electrolyte solutions and is present in certain electrolye solutions, such as "plasmalyte A", which is used for intravenous fluid resuscitation. Gluconate is also used in a variety of pharmaceutical applications. For instance, calcium gluconate is used to treat burns arising from hydrofluoric acid while quinine gluconate is a salt of gluconic acid and quinine, which is used for intramuscular injection in the treatment of malaria. In humans, altered levels of gluconic acid have been found in the metabolic disorder called the transaldolase deficiency.
CAS Number526-95-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
2,3,4,5,6-pentahydroxy-hexanoatebiospider
2,3,4,5,6-pentahydroxy-hexanoic acidbiospider
2,3,4,5,6-Pentahydroxycaproic acidbiospider
D-gluco-HexonateGenerator
D-gluco-hexonic acidbiospider
D-gluconatebiospider
D-gluconic acidbiospider
E574manual
Gluconic acidbiospider
Gluconic acid, d-biospider
Gulonic acidbiospider
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O7
IUPAC name(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
Average Molecular Weight196.1553
Monoisotopic Molecular Weight196.058302738
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 36.74%; H 6.17%; O 57.10%DFC
Melting PointMp 130-132°DFC
Boiling PointNot Available
Experimental Water Solubility316 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKapKa 3.76 (17°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -6.7 -> +11.7 (H2O, 5 d)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0932000000-202af87cea2d1f7184abSpectrum
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-005a-0920000000-2308d9356bc5bb01420eSpectrum
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-014j-0950000000-61ab7adf15e353df4ba2Spectrum
GC-MSD-Gluconic acid, 6 TMS, GC-MS Spectrumsplash10-0le9-1964000000-5eb7d6777170e1ad5fa0Spectrum
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0932000000-202af87cea2d1f7184abSpectrum
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-0le9-1964000000-5eb7d6777170e1ad5fa0Spectrum
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0931000000-b07fcc4ac1e6701d32c8Spectrum
GC-MSD-Gluconic acid, non-derivatized, GC-MS Spectrumsplash10-0fr2-0930000000-181f7b697b591cf8080bSpectrum
Predicted GC-MSD-Gluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06tu-9500000000-ebe398c88f74bb51e702Spectrum
Predicted GC-MSD-Gluconic acid, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fr-6121297000-698854fa2453487a1d69Spectrum
Predicted GC-MSD-Gluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TBDMS_6_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, "Gluconic acid,6TBDMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Gluconic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-06vj-1900000000-78e4a5d92be678c068e42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03ds-5900000000-f5d8284baa473ce9d77f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9500000000-7c5b20eef98d0e3d6cbb2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-b2632ca9154cc5e444382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-002b-5900000000-4a3066f9dfd6653682fb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-50f63dfd017a8380a47c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-91ccf7c8949c1c9d852a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-b2632ca9154cc5e444382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-5900000000-cf9b480ac397acfebc712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-eca61f6a9c0f1d06e84d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9000000000-91ccf7c8949c1c9d852a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9000000000-3950065b4128434714342021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a6r-7900000000-5bb7335ada119405f6ad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-056r-5900000000-717fb7f30be3f6d61d462021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-6900000000-a8da6e6791f61d1543602021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052b-9500000000-a346a36e3dd0bea4abcc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-056r-9000000000-6e1dd3cd14f2b116fa7c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-42150530e3232b66059b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9500000000-763d7b03787732284c192016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9100000000-040569af699927ca68592016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ic-9800000000-3571d4f2ff79bc0d7fa02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-3cb207fadbe1fcae5cb72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-8c900935a94065d0938b2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID10240
ChEMBL IDCHEMBL464345
KEGG Compound IDC00257
Pubchem Compound ID10690
Pubchem Substance IDNot Available
ChEBI ID33198
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00625
CRC / DFC (Dictionary of Food Compounds) IDCBW08-O:CBW09-P
EAFUS ID1491
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00007303
HET IDGCO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGluconic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Probable gluconokinaseIDNKQ5T6J7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference