Cannabis Compound Database: Showing Compound Card for Gluconic acid (CDB006170)

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Record Information

Version

1.0

Created at

2020-03-18 23:22:24 UTC

Updated at

2020-12-07 19:06:58 UTC

CannabisDB ID

CDB006170

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Gluconic acid

Description

Gluconic 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‚Äôs 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.

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

196.16

Monoisotopic Molecular Weight

196.0583

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

Household products:

Antimicrobial agent:

Antimalarial

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	417 °C	Wikipedia
Water Solubility	316 mg/mL at 25 °C	MERCK INDEX (1996)
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0932000000-202af87cea2d1f7184ab	Spectrum
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-005a-0920000000-2308d9356bc5bb01420e	Spectrum
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-014j-0950000000-61ab7adf15e353df4ba2	Spectrum
GC-MS	Gluconic acid, 6 TMS, GC-MS Spectrum	splash10-0le9-1964000000-5eb7d6777170e1ad5fa0	Spectrum
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0932000000-202af87cea2d1f7184ab	Spectrum
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-0le9-1964000000-5eb7d6777170e1ad5fa0	Spectrum
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0931000000-b07fcc4ac1e6701d32c8	Spectrum
GC-MS	Gluconic acid, non-derivatized, GC-MS Spectrum	splash10-0fr2-0930000000-181f7b697b591cf8080b	Spectrum
Predicted GC-MS	Gluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06tu-9500000000-ebe398c88f74bb51e702	Spectrum
Predicted GC-MS	Gluconic acid, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03fr-6121297000-698854fa2453487a1d69	Spectrum
Predicted GC-MS	Gluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TBDMS_6_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, "Gluconic acid,6TBDMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gluconic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-06vj-1900000000-78e4a5d92be678c068e4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03ds-5900000000-f5d8284baa473ce9d77f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9500000000-7c5b20eef98d0e3d6cbb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-b2632ca9154cc5e44438	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-002b-5900000000-4a3066f9dfd6653682fb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-50f63dfd017a8380a47c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-056r-9000000000-91ccf7c8949c1c9d852a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a6r-9000000000-6e40f1cebd8b460016b3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-b2632ca9154cc5e44438	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-002b-5900000000-cf9b480ac397acfebc71	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-eca61f6a9c0f1d06e84d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-056r-9000000000-91ccf7c8949c1c9d852a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a6r-9000000000-6e40f1cebd8b460016b3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9000000000-3950065b412843471434	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a6r-7900000000-5bb7335ada119405f6ad	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-056r-5900000000-717fb7f30be3f6d61d46	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-002b-6900000000-a8da6e6791f61d154360	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052b-9500000000-a346a36e3dd0bea4abcc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9000000000-6e1dd3cd14f2b116fa7c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-2900000000-42150530e3232b66059b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9500000000-763d7b03787732284c19	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9100000000-040569af699927ca6859	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05ic-9800000000-3571d4f2ff79bc0d7fa0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9400000000-3cb207fadbe1fcae5cb7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-8c900935a94065d0938b	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H 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

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Probable gluconokinase	IDNK	9q21.32	Q5T6J7	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Regucalcin	RGN	Xp11.3	Q15493	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000625

DrugBank ID

DB13180

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

General References

Shindia AA, El-Sherbeny GA, El-Esawy AE, Sheriff YM: Production of gluconic Acid by some local fungi. Mycobiology. 2006 Mar;34(1):22-9. doi: 10.4489/MYCO.2006.34.1.022. Epub 2006 Mar 31. [PubMed:24039465 ]

Enzymes

Enzyme Details

1. Probable gluconokinase

General function:: Involved in shikimate kinase activity
Specific function:: Not Available
Gene Name:: IDNK
Uniprot ID:: Q5T6J7
Molecular weight:: 20577.63

Showing Compound Card for Gluconic acid (CDB006170)

Structure for CDB006170 (Gluconic acid)

Enzymes