P. aeruginosa Metabolome Database: Gluconolactone (PAMDB000057)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000057

Identification

Name:

Gluconolactone

Description:

Gluconolactone is a lactone or oxidized derivative of glucose. Gluconolactone is a polyhydroxy acid (PHA) that is capable of chelating metals and may also function by scavenging free radicals. When dissolved in water, it is partially hydrolysed to gluconic acid, with the balance between the lactone form and the acid form established as a chemical equilibrium. The rate of hydrolysis of gluconolactone is increased by heat and high pH. It is an intermediate in glucose and glucose-1-phosphate degradation.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

δ-gluconolactone
1,5-D-Gluconolactone
1,5-delta-Gluconolactone
1,5-Gluconolactone
1,5-δ-Gluconolactone
3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one
3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
b-glucono-1,5-Lactone
Beta-Glucono-1,5-Lactone
D(+)-Gluconate g-lactone
D(+)-Gluconate gamma-lactone
D(+)-Gluconate γ-lactone
D(+)-Gluconic acid g-lactone
D(+)-Gluconic acid gamma-lactone
D(+)-Gluconic acid γ-lactone
D-(+)-Gluconate D-lactone
D-(+)-Gluconate-delta lactone
D-(+)-Gluconate-δ lactone
D-(+)-Gluconic acid D-lactone
D-(+)-Gluconic acid-delta lactone
D-(+)-Gluconic acid-δ lactone
D-Aldonolactone
D-delta-Gluconolactone
D-Gluconate 1,5-lactone
D-Gluconate D-lactone
D-Gluconate delta-lactone
D-Gluconate lactone
D-Gluconate δ-lactone
D-Gluconate-1,5-lactone
D-Gluconate-delta-lactone
D-Gluconate-δ-lactone
D-Gluconic acid 1,5-lactone
D-Gluconic acid D-lactone
D-Gluconic acid delta-lactone
D-Gluconic acid lactone
D-Gluconic acid δ-lactone
D-Gluconic acid-1,5-lactone
D-Gluconic acid-delta-lactone
D-Gluconic acid-δ-lactone
D-Gluconic delta-lactone
D-Gluconic δ-lactone
D-glucono-δ-lactone
D-Glucono-1,5-lactone
D-Glucono-D-lactone
D-Glucono-delta-lactone
D-glucono-δ-Lactone
D-Gluconolactone
D-δ-Gluconolactone
Delta-(+)-Gluconate D-lactone
Delta-(+)-Gluconate-delta lactone
Delta-(+)-Gluconic acid D-lactone
Delta-(+)-Gluconic acid-delta lactone
Delta-Aldonolactone
Delta-D-Gluconolactone
Delta-delta-Gluconolactone
Delta-Gluconate 1,5-lactone
Delta-Gluconate D-lactone
Delta-Gluconate delta-lactone
Delta-Gluconate lactone
Delta-Gluconate-1,5-lactone
delta-Gluconate-delta-lactone
Delta-Gluconic acid 1,5-lactone
Delta-Gluconic acid D-lactone
Delta-Gluconic acid delta-lactone
Delta-Gluconic acid lactone
Delta-Gluconic acid-1,5-lactone
Delta-Gluconic acid-delta-lactone
Delta-Gluconic delta-lactone
Delta-Glucono-1,5-lactone
Delta-Glucono-delta-lactone
Delta-Gluconolactone
Fujiglucon
g-Gluconolactone
Gamma-Gluconolactone
Glucarolactone
Gluconate lactone
Gluconate, lactone
Gluconic acid lactone
Gluconic acid, lactone
Gluconic delta-lactone
Gluconic lactone
Gluconic δ-lactone
Glucono 1,5-lactone
Glucono delta lactone
Glucono delta-lactone
glucono g-Lactone
Glucono gamma-lactone
glucono γ-Lactone
glucono δ Lactone
glucono δ-Lactone
Glucono-δ-lactone
Glucono-1,5-lactone
Glucono-delta-lactone
glucono-δ-Lactone
Gluconolactone
β-glucono-1,5-Lactone
γ-Gluconolactone
δ-(+)-Gluconate D-lactone
δ-(+)-Gluconate-δ lactone
δ-(+)-Gluconic acid D-lactone
δ-(+)-Gluconic acid-δ lactone
δ-Aldonolactone
δ-D-Gluconolactone
δ-Gluconate 1,5-lactone
δ-Gluconate D-lactone
δ-Gluconate lactone
δ-Gluconate δ-lactone
δ-Gluconate-1,5-lactone
δ-Gluconate-δ-lactone
δ-Gluconic acid 1,5-lactone
δ-Gluconic acid D-lactone
δ-Gluconic acid lactone
δ-Gluconic acid δ-lactone
δ-Gluconic acid-1,5-lactone
δ-Gluconic acid-δ-lactone
δ-Gluconic δ-lactone
δ-glucono-1,5-Lactone
δ-glucono-δ-Lactone
δ-Gluconolactone
δ-δ-Gluconolactone

Chemical Formula:

C₆H₁₀O₆

Average Molecular Weight:

178.14

Monoisotopic Molecular Weight:

178.047738052

InChI Key:

PHOQVHQSTUBQQK-SQOUGZDYSA-N

InChI:

InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

CAS number:

90-80-2

IUPAC Name:

(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one

Traditional IUPAC Name:

gluconolactone

SMILES:

OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Monosaccharides

Direct Parent

Gluconolactones

Alternative Parents

Substituents

Gluconolactone
Delta_valerolactone
Delta valerolactone
Oxane
Secondary alcohol
Polyol
Lactone
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

aldono-1,5-lactone (CHEBI:16217 )
gluconolactone (CHEBI:16217 )

Physical Properties

State:

Solid

Charge:

Melting point:

151-155 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	590.0 mg/mL [MERCK INDEX (1996)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	586.0 mg/mL	ALOGPS
logP	-2.2	ALOGPS
logP	-2.7	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.78 m³·mol^-1	ChemAxon
Polarizability	15.63 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8
b-D-Glucose + a ubiquinone > Gluconolactone + a ubiquinol
Gluconolactone + Water > Hydrogen ion + Gluconic acid
Gluconolactone + Hydrogen ion <> b-D-Glucose
D-Glucose + Ubiquinone-10 > Gluconolactone + Ubiquinol-1

Pathways:

Microbial metabolism in diverse environments pae01120
Pentose phosphate pathway pae00030

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)	splash10-0002-0932000000-0b9d34fd1930d30adac9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-005a-0920000000-48470ef74f46934597a0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-014j-0950000000-483acf515b56ae5dc886	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0fvi-1952000000-f92fb779cdb5daa45f09	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-001i-5900000000-443ab6dcdad04641cb49	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0avl-9000000000-5aba2e27767b74e7e315	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-052f-9000000000-081648ead7bc8b21d941	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Friedrich T, Strohdeicher M, Hofhaus G, Preis D, Sahm H, Weiss H: The same domain motif for ubiquinone reduction in mitochondrial or chloroplast NADH dehydrogenase and bacterial glucose dehydrogenase. FEBS Lett. 1990 Jun 4;265(1-2):37-40. Pubmed: 2142103
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
Hunt MJ, Barnetson RS: A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne. Australas J Dermatol. 1992;33(3):131-4. Pubmed: 1303072
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
MacNeil ML, Steinberg KK, Yeager PR, Smith SJ: A semiautomated procedure for urinary D-glucaric acid using a centrifugal analyzer. J Anal Toxicol. 1986 Jan-Feb;10(1):15-7. Pubmed: 3951202
Puri RN, Zhou FX, Colman RF, Colman RW: Plasmin-induced platelet aggregation is accompanied by cleavage of aggregin and indirectly mediated by calpain. Am J Physiol. 1990 Dec;259(6 Pt 1):C862-8. Pubmed: 2148055
Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84. Pubmed: 1797843
Steinberg KK, Needham LL: A comparison of two methods for quantifying D-glucaric acid. J Anal Toxicol. 1986 Jul-Aug;10(4):139-41. Pubmed: 3747452
van Weely S, Brandsma M, Strijland A, Tager JM, Aerts JM: Demonstration of the existence of a second, non-lysosomal glucocerebrosidase that is not deficient in Gaucher disease. Biochim Biophys Acta. 1993 Mar 24;1181(1):55-62. Pubmed: 8457606
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Chu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16217
HMDB ID	HMDB00150
Pubchem Compound ID	7027
Kegg ID	C00198
ChemSpider ID	6760
Wikipedia	Gluconolactone
BioCyc ID	GLC-D-LACTONE
EcoCyc ID	GLC-D-LACTONE
Ligand Expo	LGC

Gluconolactone (PAMDB000057)

Structure for Gluconolactone (PAMDB000057)