Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:34 UTC

HMDB ID

HMDB0000150

Secondary Accession Numbers

HMDB00150

Metabolite Identification

Common Name

Gluconolactone

Description

Gluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one	ChEBI
1,5-D-Gluconolactone	ChEBI
1,5-Gluconolactone	ChEBI
D-Aldonolactone	ChEBI
D-Gluconic acid delta-lactone	ChEBI
D-Gluconic acid lactone	ChEBI
D-Gluconolactone	ChEBI
D-threo-aldono-1,5-Lactone	ChEBI
delta-D-Gluconolactone	ChEBI
delta-Gluconolactone	ChEBI
Glucarolactone	ChEBI
Gluconic acid lactone	ChEBI
Gluconic delta-lactone	ChEBI
Gluconic lactone	ChEBI
D-Gluconate delta-lactone	Generator
D-Gluconate δ-lactone	Generator
D-Gluconic acid δ-lactone	Generator
D-Gluconate lactone	Generator
δ-D-gluconolactone	Generator
δ-Gluconolactone	Generator
Gluconate lactone	Generator
Gluconic δ-lactone	Generator
1,5-delta-Gluconolactone	HMDB
3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one	HMDB
D-(+)-Gluconic acid D-lactone	HMDB
D-(+)-Gluconic acid-delta lactone	HMDB
D-delta-Gluconolactone	HMDB
D-Gluconic acid 1,5-lactone	HMDB
D-Gluconic acid D-lactone	HMDB
D-Gluconic acid-1,5-lactone	HMDB
D-Gluconic acid-delta-lactone	HMDB
D-Gluconic delta-lactone	HMDB
D-Glucono-1,5-lactone	HMDB
D-glucono-D-Lactone	HMDB
delta-(+)-Gluconic acid D-lactone	HMDB
delta-Aldonolactone	HMDB
delta-Gluconic acid 1,5-lactone	HMDB
delta-Gluconic acid D-lactone	HMDB
delta-Gluconic acid lactone	HMDB
delta-Gluconic acid-1,5-lactone	HMDB
delta-Glucono-1,5-lactone	HMDB
Fujiglucon	HMDB
Gluconate, lactone	HMDB
Glucono 1,5-lactone	HMDB
Glucono delta lactone	HMDB
Glucono delta-lactone	HMDB
GDL (Gluconate)	MeSH, HMDB
Glucono-delta-lactone	MeSH
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one	HMDB
D-(+)-Gluconic acid delta-lactone	HMDB
D-(+)-Gluconic acid δ-lactone	HMDB
D-(+)-Glucono-1,5-lactone	HMDB
D-(+)-Glucono-delta-lactone	HMDB
D-(+)-Glucono-δ-lactone	HMDB
D-(+)-Glucose delta-lactone	HMDB
D-(+)-Glucose δ-lactone	HMDB
D-Glucono-delta-lactone	HMDB
D-Glucono-δ-lactone	HMDB
Glucono-δ-lactone	HMDB
Gluconolactone	HMDB
Lysactone	HMDB

Chemical Formula

C₆H₁₀O₆

Average Molecular Weight

178.14

Monoisotopic Molecular Weight

178.047738052

IUPAC Name

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

Traditional Name

gluconolactone

CAS Registry Number

90-80-2

SMILES

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

InChI Identifier

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

InChI Key

PHOQVHQSTUBQQK-SQOUGZDYSA-N

Chemical Taxonomy

Description

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

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Gluconolactones

Alternative Parents

Substituents

Gluconolactone
Delta valerolactone
Delta_valerolactone
Oxane
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

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

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	151 - 155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	590 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	130.589	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000372
[M+H]+	Not Available	127.642	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000372

Predicted Molecular Properties

Property	Value	Source
Water Solubility	586 g/L	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	15.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.747	31661259
DarkChem	[M-H]-	133.245	31661259
AllCCS	[M+H]+	139.869	32859911
AllCCS	[M-H]-	130.82	32859911
DeepCCS	[M+H]+	138.21	30932474
DeepCCS	[M-H]-	135.817	30932474
DeepCCS	[M-2H]-	170.244	30932474
DeepCCS	[M+Na]+	144.557	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	131.8	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gluconolactone	OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O	3157.3	Standard polar	33892256
Gluconolactone	OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O	1752.4	Standard non polar	33892256
Gluconolactone	OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O	1668.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gluconolactone,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O	1668.7	Semi standard non polar	33892256
Gluconolactone,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C(=O)O[C@H](CO)[C@@H](O)[C@@H]1O	1680.4	Semi standard non polar	33892256
Gluconolactone,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](O)C(=O)O[C@H](CO)[C@H]1O	1679.8	Semi standard non polar	33892256
Gluconolactone,1TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O	1663.2	Semi standard non polar	33892256
Gluconolactone,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	1722.4	Semi standard non polar	33892256
Gluconolactone,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1718.1	Semi standard non polar	33892256
Gluconolactone,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	1716.0	Semi standard non polar	33892256
Gluconolactone,2TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[C@@H]1CO	1712.7	Semi standard non polar	33892256
Gluconolactone,2TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)C(=O)O[C@H](CO)[C@H]1O	1701.1	Semi standard non polar	33892256
Gluconolactone,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C	1694.8	Semi standard non polar	33892256
Gluconolactone,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1769.7	Semi standard non polar	33892256
Gluconolactone,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1793.1	Semi standard non polar	33892256
Gluconolactone,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1770.8	Semi standard non polar	33892256
Gluconolactone,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)C(=O)O[C@H](CO)[C@H]1O[Si](C)(C)C	1760.9	Semi standard non polar	33892256
Gluconolactone,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1839.8	Semi standard non polar	33892256
Gluconolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O	1922.6	Semi standard non polar	33892256
Gluconolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C(=O)O[C@H](CO)[C@@H](O)[C@@H]1O	1941.3	Semi standard non polar	33892256
Gluconolactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)C(=O)O[C@H](CO)[C@H]1O	1929.1	Semi standard non polar	33892256
Gluconolactone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O	1921.9	Semi standard non polar	33892256
Gluconolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2201.1	Semi standard non polar	33892256
Gluconolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2204.7	Semi standard non polar	33892256
Gluconolactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2185.5	Semi standard non polar	33892256
Gluconolactone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H]1CO	2195.3	Semi standard non polar	33892256
Gluconolactone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@H](CO)[C@H]1O	2178.5	Semi standard non polar	33892256
Gluconolactone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2183.8	Semi standard non polar	33892256
Gluconolactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2474.2	Semi standard non polar	33892256
Gluconolactone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2485.9	Semi standard non polar	33892256
Gluconolactone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2471.6	Semi standard non polar	33892256
Gluconolactone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C	2455.4	Semi standard non polar	33892256
Gluconolactone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2701.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Gluconolactone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0932000000-0b9d34fd1930d30adac9	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Gluconolactone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-005a-0920000000-48470ef74f46934597a0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Gluconolactone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014j-0950000000-483acf515b56ae5dc886	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Gluconolactone GC-MS (4 TMS)	splash10-0fvi-1952000000-f92fb779cdb5daa45f09	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized)	splash10-0fvi-1952000000-f92fb779cdb5daa45f09	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-11bi-9500000000-59fc28b889280c7c2a5c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (4 TMS) - 70eV, Positive	splash10-0kki-7239300000-aa269ca53fc88c5847e7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gluconolactone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-001i-5900000000-443ab6dcdad04641cb49	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0avl-9000000000-5aba2e27767b74e7e315	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-052f-9000000000-081648ead7bc8b21d941	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 10V, Negative-QTOF	splash10-054t-9200000000-f80b44237ec36658430a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 28V, Negative-QTOF	splash10-004i-9800000000-3c2752fe8b35c2f72850	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 20V, Negative-QTOF	splash10-0ab9-9000000000-05bc27806ac72dbcec47	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 40V, Negative-QTOF	splash10-052f-9000000000-1f7ea9822812efafd66e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 35V, Negative-QTOF	splash10-0002-9000000000-32e4789569e5ebdb0a57	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 40V, Positive-QTOF	splash10-0006-9000000000-5c93d1197ecefd3faca0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 20V, Positive-QTOF	splash10-0avj-9000000000-56d207c80751c4bc3c09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gluconolactone 10V, Positive-QTOF	splash10-06ei-9300000000-b4b9842c0062ae80b789	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 10V, Positive-QTOF	splash10-01t9-0900000000-7a99fa6e5ac000ab06f1	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 20V, Positive-QTOF	splash10-03fu-3900000000-7f96bedb201e601e238e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 40V, Positive-QTOF	splash10-006x-9200000000-c51e82de843b7755c5b6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 10V, Negative-QTOF	splash10-004i-3900000000-b80e81f6d02c1d0116a2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 20V, Negative-QTOF	splash10-0adi-6900000000-590a75b51bd97402a88d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 40V, Negative-QTOF	splash10-052f-9000000000-ea7b9a23b7a07d266c68	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 10V, Positive-QTOF	splash10-01tc-0900000000-061a17370d3f9bfa1c13	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 20V, Positive-QTOF	splash10-01tl-9500000000-549c20b0fb39634d8731	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 40V, Positive-QTOF	splash10-08mm-9100000000-44352cf8b9847abddc99	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 10V, Negative-QTOF	splash10-004i-0900000000-4498d74e012d572e6493	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 20V, Negative-QTOF	splash10-0a6r-6900000000-2d15c7e5cc6967914c93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gluconolactone 40V, Negative-QTOF	splash10-0abc-9000000000-1f0b910b13e645939f4c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
pentose phosphate pathway	Not Available	Not Available
Glucose-6-phosphate dehydrogenase deficiency		Not Available
Ribose-5-phosphate isomerase deficiency		Not Available
Transaldolase deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.5 (0.0-1.0) uM	Adult (>18 years old)	Both	Prostate Cancer	19212411	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Prostate cancer

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 ]

Associated OMIM IDs

176807 (Prostate cancer)

External Links

DrugBank ID

DB04564

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001245

KNApSAcK ID

Not Available

Chemspider ID

6760

KEGG Compound ID

C00198

BioCyc ID

GLC-D-LACTONE

BiGG ID

Not Available

Wikipedia Link

Gluconolactone

METLIN ID

353

PubChem Compound

7027

PDB ID

Not Available

ChEBI ID

16217

Food Biomarker Ontology

Not Available

VMH ID

G15LAC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Enzymes

Enzyme Details

1. 6-phosphogluconolactonase

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:: PGLS
Uniprot ID:: O95336
Molecular weight:: 27546.495

Enzyme Details

2. Glucose-6-phosphate 1-dehydrogenase

General function:: Involved in glucose-6-phosphate dehydrogenase activity
Specific function:: Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:: G6PD
Uniprot ID:: P11413
Molecular weight:: 62467.88

Enzyme Details

3. GDH/6PGL endoplasmic bifunctional protein

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: Oxidizes glucose-6-phosphate and glucose, as well as other hexose-6-phosphates.
Gene Name:: H6PD
Uniprot ID:: O95479
Molecular weight:: 88891.99

Reactions

D-Glucose + NAD(P)(+) → Gluconolactone + NAD(P)H	details

Enzyme Details

4. Glycogen phosphorylase, liver form

General function:: Involved in phosphorylase activity
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGL
Uniprot ID:: P06737
Molecular weight:: 93133.25

Enzyme Details

5. Glycogen phosphorylase, muscle form

General function:: Involved in phosphorylase activity
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGM
Uniprot ID:: P11217
Molecular weight:: 87316.355

Enzyme Details

6. Glycogen phosphorylase, brain form

General function:: Involved in phosphorylase activity
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGB
Uniprot ID:: P11216
Molecular weight:: 96695.18

Enzyme Details

7. 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

Showing metabocard for Gluconolactone (HMDB0000150)

MOL for HMDB0000150 (Gluconolactone)

3D MOL for HMDB0000150 (Gluconolactone)

3D SDF for HMDB0000150 (Gluconolactone)

3D-SDF for HMDB0000150 (Gluconolactone)

PDB for HMDB0000150 (Gluconolactone)

3D PDB for HMDB0000150 (Gluconolactone)

SMILES for HMDB0000150 (Gluconolactone)

INCHI for HMDB0000150 (Gluconolactone)

Structure for HMDB0000150 (Gluconolactone)

3D Structure for HMDB0000150 (Gluconolactone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions