Human Metabolome Database: Showing metabocard for Gluconic acid (HMDB0000625)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-11-09 23:13:55 UTC

HMDB ID

HMDB0000625

Secondary Accession Numbers

HMDB0003373
HMDB00625
HMDB03373

Metabolite Identification

Common Name

Gluconic acid

Description

Gluconic acid, also known as D-gluconate or D-glukonsaeure, 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 a drug which is used for use as part of electrolyte supplementation in total parenteral nutrition [fda label]. It is also used in cleaning products where it helps cleaning up mineral deposits. The salts of gluconic acid are known as "gluconates". Gluconic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gluconic acid or Gluconic acid is used to maintain the cation-anion balance on electrolyte solutions. Gluconic acid exists in all living species, ranging from bacteria to humans. In humans, gluconic acid is involved in the metabolic disorder called the transaldolase deficiency pathway. Outside of the human body, Gluconic acid has been detected, but not quantified in, milk (cow). This could make gluconic acid a potential biomarker for the consumption of these foods. 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). It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. Gluconic acid occurs naturally in fruit, honey, kombucha tea, and wine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid	ChEBI
D-Gluco-hexonic acid	ChEBI
D-Gluconsaeure	ChEBI
D-Glukonsaeure	ChEBI
Dextronic acid	ChEBI
Glycogenic acid	ChEBI
Hexonic acid	ChEBI
Maltonic acid	ChEBI
D-Gluconate	Kegg
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoate	Generator
D-Gluco-hexonate	Generator
Dextronate	Generator
Glycogenate	Generator
Hexonate	Generator
Maltonate	Generator
D-Gluconic acid	Generator
Gluconate	Generator
2,3,4,5,6-Pentahydroxy-hexanoate	HMDB
2,3,4,5,6-Pentahydroxy-hexanoic acid	HMDB
2,3,4,5,6-Pentahydroxyhexanoate	HMDB
2,3,4,5,6-Pentahydroxyhexanoic acid	HMDB
GCO	HMDB
Glosanto	HMDB
Glyconate	HMDB
Glyconic acid	HMDB
Pentahydroxycaproate	HMDB
Pentahydroxycaproic acid	HMDB
Boron gluconate	HMDB
Gluconic acid, (113)indium-labeled	HMDB
Gluconic acid, calcium salt	HMDB
Gluconic acid, cesium(+3) salt	HMDB
Gluconic acid, lanthanum(+3) salt	HMDB
Gluconic acid, sodium salt	HMDB
Gluconic acid, strontium (2:1) salt	HMDB
Magnerot	HMDB
Manganese gluconate	HMDB
Sodium gluconate	HMDB
Zinc gluconate	HMDB
Gluconic acid, (159)dysprosium-labeled salt	HMDB
Gluconic acid, aluminum (3:1) salt	HMDB
Gluconic acid, ammonium salt	HMDB
Gluconic acid, magnesium (2:1) salt	HMDB
Gluconic acid, (14)C-labeled	HMDB
Gluconic acid, 1-(14)C-labeled	HMDB
Gluconic acid, 6-(14)C-labeled	HMDB
Gluconic acid, cobalt (2:1) salt	HMDB
Gluconic acid, copper salt	HMDB
Gluconic acid, manganese (2:1) salt	HMDB
Gluconic acid, potassium salt	HMDB
Gluconic acid, tin(+2) salt	HMDB
Gluconic acid, zinc salt	HMDB
Lithium gluconate	HMDB
Magnesium gluconate	HMDB
Gluconic acid, (99)technecium (5+) salt	HMDB
Gluconic acid, fe(+2) salt, dihydrate	HMDB
Gluconic acid, monolithium salt	HMDB
Gluconic acid, monopotassium salt	HMDB
Gluconic acid, monosodium salt	HMDB

Chemical Formula

C₆H₁₂O₇

Average Molecular Weight

196.1553

Monoisotopic Molecular 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

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar 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 Framework

Aliphatic acyclic compounds

External Descriptors

gluconic acid (CHEBI:33198 )
Uronic acids (C00257 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Source:

Endogenous

Biological:

Fungi:

Aspergillus

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Chelating agent

Pharmaceutical industry:

Pharmaceutical

Food and nutrition:

Sequestrant

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	113 - 118 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	316 mg/mL at 25 °C	MERCK INDEX (1996)
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	159 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.4	ChemAxon
logS	-0.09	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.27 m³·mol⁻¹	ChemAxon
Polarizability	17.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0932000000-202af87cea2d1f7184ab	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-005a-0920000000-2308d9356bc5bb01420e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014j-0950000000-61ab7adf15e353df4ba2	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0le9-1964000000-5eb7d6777170e1ad5fa0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0932000000-202af87cea2d1f7184ab	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0le9-1964000000-5eb7d6777170e1ad5fa0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0931000000-b07fcc4ac1e6701d32c8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-0930000000-181f7b697b591cf8080b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tu-9500000000-ebe398c88f74bb51e702	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive	splash10-03fr-6121297000-698854fa2453487a1d69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-06vj-1900000000-78e4a5d92be678c068e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03ds-5900000000-f5d8284baa473ce9d77f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9500000000-7c5b20eef98d0e3d6cbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-b2632ca9154cc5e44438	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-002b-5900000000-4a3066f9dfd6653682fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-50f63dfd017a8380a47c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-056r-9000000000-91ccf7c8949c1c9d852a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a6r-9000000000-6e40f1cebd8b460016b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-b2632ca9154cc5e44438	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-002b-5900000000-cf9b480ac397acfebc71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-eca61f6a9c0f1d06e84d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-056r-9000000000-91ccf7c8949c1c9d852a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-9000000000-6e40f1cebd8b460016b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-2900000000-42150530e3232b66059b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9500000000-763d7b03787732284c19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9100000000-040569af699927ca6859	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05ic-9800000000-3571d4f2ff79bc0d7fa0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9400000000-3cb207fadbe1fcae5cb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-8c900935a94065d0938b	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta
Prostate

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<5 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	3.295 +/- 0.534 uM	Adult (>18 years old)	Both	Normal	24713860	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	45.49 +/- 24.12 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	13.3 (8.2-26.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	35.0+/-29.0 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	21.5 (8.1-38.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	63.463 +/- 28.036 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.732 +/- 0.687 uM	Adult (>18 years old)	Both	Schizophrenia	24713860	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cryptosporidium infection	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	65.277 +/- 47.794 umol/mmol creatinine	Children (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 ]
Colorectal cancer
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 ] 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
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

181500 (Schizophrenia)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB13180

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Gluconic_acid

METLIN ID

345

PubChem Compound

10690

PDB ID

Not Available

ChEBI ID

33198

Food Biomarker Ontology

Not Available

VMH ID

GLCN

MarkerDB ID

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

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 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Regucalcin

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

Enzyme Details

2. Probable gluconokinase

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

Showing metabocard for Gluconic acid (HMDB0000625)

Structure for HMDB0000625 (Gluconic acid)

Enzymes

Reactions

Reactions