| Common Name |
Gluconic acid
| Description |
Gluconic acid occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regliator. 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.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(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
(2R,3S,4R,5R)-2,3,4,5,6-PentahydroxyhexanoateGenerator
GluconateGenerator
D-gluco-HexonateGenerator
DextronateGenerator
GlycogenateGenerator
HexonateGenerator
MaltonateGenerator
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
D-GluconateHMDB
D-Gluconic acidHMDB
GCOHMDB
GlosantoHMDB
GlyconateHMDB
Glyconic acidHMDB
PentahydroxycaproateHMDB
Pentahydroxycaproic acidHMDB
Boron gluconateMeSH
Gluconic acid, (113)indium-labeledMeSH
Gluconic acid, calcium saltMeSH
Gluconic acid, cesium(+3) saltMeSH
Gluconic acid, lanthanum(+3) saltMeSH
Gluconic acid, sodium saltMeSH
Gluconic acid, strontium (2:1) saltMeSH
MagnerotMeSH
Manganese gluconateMeSH
Sodium gluconateMeSH
Zinc gluconateMeSH
Gluconic acid, (159)dysprosium-labeled saltMeSH
Gluconic acid, aluminum (3:1) saltMeSH
Gluconic acid, ammonium saltMeSH
Gluconic acid, magnesium (2:1) saltMeSH
Gluconic acid, (14)C-labeledMeSH
Gluconic acid, 1-(14)C-labeledMeSH
Gluconic acid, 6-(14)C-labeledMeSH
Gluconic acid, cobalt (2:1) saltMeSH
Gluconic acid, copper saltMeSH
Gluconic acid, manganese (2:1) saltMeSH
Gluconic acid, potassium saltMeSH
Gluconic acid, tin(+2) saltMeSH
Gluconic acid, zinc saltMeSH
Lithium gluconateMeSH
Magnesium gluconateMeSH
Gluconic acid, (99)technecium (5+) saltMeSH
Gluconic acid, fe(+2) salt, dihydrateMeSH
Gluconic acid, monolithium saltMeSH
Gluconic acid, monopotassium saltMeSH
Gluconic acid, monosodium saltMeSH
| Chemical Formlia |
C6H12O7
| Average Molecliar Weight |
196.1553
| Monoisotopic Molecliar Weight |
196.058302738
| IUPAC Name |
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
| Traditional Name |
gluconate
| CAS Registry Number |
526-95-4
| 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 Key |
RGHNJXZEOKUKBD-SQOUGZDYSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point113 – 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility316 mg/mL at 25 °CMERCK INDEX (1996)
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Polarizability17.15 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0932000000-202af87cea2d1f7184abView in MoNA
| GC-MS |
GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-005a-0920000000-2308d9356bc5bb01420eView in MoNA
| GC-MS |
GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014j-0950000000-61ab7adf15e353df4ba2View in MoNA
| GC-MS |
GC-MS Spectrum – GC-MS (6 TMS)splash10-0le9-1964000000-5eb7d6777170e1ad5fa0View in MoNA
| Predicted GC-MS |
Predicted GC-MS Spectrum – GC-MSNot Available
| GC-MS |
GC-MS Spectrum – GC-EI-TOFsplash10-0002-0931000000-b07fcc4ac1e6701d32c8View in MoNA
| GC-MS |
GC-MS Spectrum – GC-EI-TOFsplash10-0002-0931000000-b07fcc4ac1e6701d32c8View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-06vj-1900000000-78e4a5d92be678c068e4View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-03ds-5900000000-f5d8284baa473ce9d77fView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9500000000-7c5b20eef98d0e3d6cbbView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-b2632ca9154cc5e44438View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-002b-5900000000-4a3066f9dfd6653682fbView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-50f63dfd017a8380a47cView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-91ccf7c8949c1c9d852aView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b3View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-002b-5900000000-cf9b480ac397acfebc71View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-004i-9000000000-eca61f6a9c0f1d06e84dView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 1D NMR |
13C NMR SpectrumNot Available
| 2D NMR |
[1H,1H] 2D NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm (predicted from logP)
| Biofluid Locations |
Blood
Feces
Saliva
Urine
| Tissue Location |
Prostate
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified<5 uMAdlit (>18 years old)BothNormal
21359215
details
BloodDetected and Quantified3.295 +/- 0.534 uMAdlit (>18 years old)Both
Normal
24713860
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
22944170
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
20669995
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Both
Normal
Zerihun T. Dame, …
details
SalivaDetected and Quantified45.49 +/- 24.12 uMAdlit (>18 years old)BothNormal
Zerihun T. Dame, …
details
UrineDetected and Quantified13.3 (8.2-26.4) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified35.0+/-29.0 umol/mmol creatinineInfant (0-1 year old)BothNormal
2026685
details
UrineDetected but not Quantified Adlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified21.5 (8.1-38.8) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified63.463 +/- 28.036 umol/mmol creatinineChildren (1 – 13 years old)Not Specified
Normal
Mordechai, Hien, …
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified3.732 +/- 0.687 uMAdlit (>18 years old)Both
Schizophrenia
24713860
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Cryptosporidium infection
22944170
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 |
- 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 ]
| Associated OMIM IDs |
181500 (Schizophrenia)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB001980
| KNApSAcK ID |
C00007303
| Chemspider ID |
10240
| KEGG Compound ID |
C00257
| BioCyc ID |
GLUCONATE
| BiGG ID |
Not Available
| Wikipedia Link |
Gluconic acid
| NuGOwiki Link |
HMDB00625
| Metagene Link |
HMDB00625
| METLIN ID |
345
| PubChem Compound |
10690
| PDB ID |
GCO
| ChEBI ID |
33198
Product: N-563
References |
| Synthesis Reference |
Anastassiadis, 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 |
- 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 ]
- 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 acid |
details |
- 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 acid |
details |
PMID: 11389700