Showing Compound D-Gluconic acid (FDB001980)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:11 UTC

Update date

2020-09-17 15:42:27 UTC

Primary ID

FDB001980

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-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.

CAS Number

526-95-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoate	Generator
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid	ChEBI
2,3,4,5,6-Pentahydroxy-hexanoate	HMDB
2,3,4,5,6-pentahydroxy-hexanoate	biospider
2,3,4,5,6-Pentahydroxy-hexanoic acid	HMDB
2,3,4,5,6-pentahydroxy-hexanoic acid	biospider
2,3,4,5,6-Pentahydroxycaproic acid	biospider
2,3,4,5,6-Pentahydroxyhexanoate	HMDB
2,3,4,5,6-Pentahydroxyhexanoic acid	HMDB
Boron gluconate	HMDB

Showing 1 to 10 of 69 entries

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

Chemical Formula

C6H12O7

IUPAC name

(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

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

Isomeric SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O

Average Molecular Weight

196.1553

Monoisotopic Molecular Weight

196.058302738

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.

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:

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Chelating agent

Pharmaceutical industry:

Pharmaceutical

Food and nutrition:

Sequestrant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	pKa 3.76 (17°)	DFC
Experimental Water Solubility	316 mg/mL at 25 oC	MERCK INDEX (1996)
Isoelectric point	Not Available
Mass Composition	C 36.74%; H 6.17%; O 57.10%	DFC
Melting Point	Mp 130-132°	DFC
Optical Rotation	[a]20D -6.7 -> +11.7 (H2O, 5 d)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

33198

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00625

CRC / DFC (Dictionary of Food Compounds) ID

CBW08-O:CBW09-P

EAFUS ID

1491

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00007303

HET ID

GCO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Gluconic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Grape wine	600.000 - 600.000 mg/L	600.000 mg/L	MANUAL
Milk (Cow)	Expected but not quantified	Not Available	23438684, 25108860
Abiyuch	Expected but not quantified	Not Available	HMDB
Acerola	Expected but not quantified	Not Available	HMDB
Acorn	Expected but not quantified	Not Available	HMDB
Acorn squash	Expected but not quantified	Not Available	HMDB
Adzuki bean	Expected but not quantified	Not Available	HMDB
Agave	Expected but not quantified	Not Available	HMDB
Alaska blueberry	Expected but not quantified	Not Available	HMDB
Alaska wild rhubarb	Expected but not quantified	Not Available	HMDB