MiMeDB: Showing metabocard for Diketogulonic acid (MMDBc0047946)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:18:03 UTC

Update Date

2024-04-30 20:33:23 UTC

Metabolite ID

MMDBc0047946

Metabolite Identification

Common Name

Diketogulonic acid

Description

Diketogulonic acid (DKG) is a metabolite of the degradation of vitamin C, the nonenzymatic hydrolysis-product of dehydroascorbate. Dehydroascorbate can be reduced back to ascorbate or hydrolyzed to DKG; the latter reaction is irreversible and DKG is devoid of antiscorbutic activity. The degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. DKG appears in human urine and represents approximately 20% of the vitamin C by-products (oxalate being approximately 44% and dehydroascorbate 20%). A major catabolic event in man is the cleavage of the molecule (presumably a spontaneous cleavage of DKG) between C2 and C3, with little if any decarboxylation. The oxalate formed in this way may contribute to the formation of kidney stones in susceptible individuals. However, the association between ascorbate supplementation and increased risk of kidney stone formation remains a matter of controversy. (PMID: 16698813 , 17222174 )

Structure

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

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0      30.699  -5.929   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      32.033  -9.779   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      28.032  -7.468   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      33.366  -5.929   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      34.700  -9.779   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.367  -8.239   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      36.033  -5.929   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      30.699  -7.468   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.033  -8.239   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.365  -8.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.366  -7.468   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.700  -8.239   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.033  -7.468   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7   13                                                            
CONECT    8    1    9   10                                                  
CONECT    9    2    8   11                                                  
CONECT   10    3    8                                                       
CONECT   11    4    9   12                                                  
CONECT   12    5   11   13                                                  
CONECT   13    6    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoic acid	ChEBI
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoate	ChEBI
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid	ChEBI
2,3-Diketo-L-gulonate	ChEBI
2,3-Diketo-L-gulonic acid	ChEBI
2,3-Dioxo-2,3-dideoxy-L-gulonic acid	ChEBI
2,3-L-Diketogulonic acid	ChEBI
Diketo-L-gulonic acid	ChEBI
L-Threo-(2,3)-hexodiulosonsaeure	ChEBI
L-Threo-2,3-hexodiurosonic acid	ChEBI
Threo-2,3-hexodiulosonic acid	ChEBI
(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoate	Generator
2,3-Dioxo-2,3-dideoxy-L-gulonate	Generator
2,3-L-Diketogulonate	Generator
Diketo-L-gulonate	Generator
L-Threo-2,3-hexodiurosonate	Generator
Threo-2,3-hexodiulosonate	Generator
Diketogulonate	Generator
2,3-Diketogulonic acid	HMDB
2,3-Dioxo-D-gulonate	HMDB
L-Threo-2,3-hexodiulosonic acid	HMDB
L-Threo-hexo-2,3-diulosonic acid	HMDB
Acid, 2,3-diketogulonic	HMDB
2,3 Diketogulonic acid	HMDB
Diketo-gulonate	HMDB
2,3-Diketogulonate	HMDB

Molecular Formula

C₆H₈O₇

Average Mass

192.1235

Monoisotopic Mass

192.02700261

IUPAC Name

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

Traditional Name

diketogulonic acid

CAS Registry Number

3409-57-2

SMILES

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

InChI Identifier

InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3+/m0/s1

InChI Key

GJQWCDSAOUMKSE-STHAYSLISA-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

Hexose monosaccharide
Medium-chain keto acid
Beta-keto acid
Sugar acid
Acyloin
Alpha-keto acid
Alpha-diketone
Beta-hydroxy ketone
Keto acid
Monosaccharide
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:15622 )
dioxo monocarboxylic acid (CHEBI:15622 )
alpha-diketone (CHEBI:15622 )
carbohydrate acid (CHEBI:15622 )
Oxo fatty acids (LMFA01060195 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	59.9 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.6	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.04 m³·mol⁻¹	ChemAxon
Polarizability	15.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nn9-9200000000-1cbed9b2b56caa085c4a	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-02or-7339800000-1615efb2d0feaa5735ea	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-1900000000-1d6c68c73855ddcddb54	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08mi-9500000000-c792fe4653b44e9ab372	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-16a4d7310299656e7744	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0g4l-9700000000-6d882e161ed0ab1a7656	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9300000000-c5167767732d60eead4b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-f6c0690482bc1a940237	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01c0-6900000000-f68a48e03dbb51e87373	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-11ou-9500000000-f51f8802520502229315	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btd-9000000000-b607173f6a4870d24b5f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005j-7900000000-095b22b39dbcc6d9fa05	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-05380c64aede8d94e31b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-84c78a8bd0634d2dfffc	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	325.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	217.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	50.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	271.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	271.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	335.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	793.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	653.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	951.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	168.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	283.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	186.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	40.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	379.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	710.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	74.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	228.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	929.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	626.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Diketogulonic acid_TMS_1	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O	standard non polar	2025-10-24	1913.04
Gas Chromatography	Diketogulonic acid_TMS_2	C[Si](C)(C)O[C@@H](CO)[C@@H](O)C(=O)C(=O)C(=O)O	standard non polar	2025-10-24	1539.89
Gas Chromatography	Diketogulonic acid_TMS_3	C[Si](C)(C)O[C@@H](C(=O)C(=O)C(=O)O)[C@@H](O)CO	standard non polar	2025-10-24	2493.26
Gas Chromatography	Diketogulonic acid_TMS_4	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@@H](O)CO	standard non polar	2025-10-24	2332.18
Gas Chromatography	Diketogulonic acid_TMS_5	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@@H](O)CO	standard non polar	2025-10-24	2043.18
Gas Chromatography	Diketogulonic acid_TMS_6	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O	standard non polar	2025-10-24	1807.04
Gas Chromatography	Diketogulonic acid_TMS_7	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	standard non polar	2025-10-24	2160.15
Gas Chromatography	Diketogulonic acid_TMS_8	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1925.95
Gas Chromatography	Diketogulonic acid_TMS_9	C[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard non polar	2025-10-24	1591.5
Gas Chromatography	Diketogulonic acid_TMS_10	C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	standard non polar	2025-10-24	1976.36
Gas Chromatography	Diketogulonic acid_TMS_11	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1787.05
Gas Chromatography	Diketogulonic acid_TMS_12	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1987.2
Gas Chromatography	Diketogulonic acid_TMS_13	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C)[C@@H](O)CO	standard non polar	2025-10-24	1637.9
Gas Chromatography	Diketogulonic acid_TMS_14	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C)[C@@H](O)CO	standard non polar	2025-10-24	1866.93
Gas Chromatography	Diketogulonic acid_TMS_15	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)[C@@H](O)CO	standard non polar	2025-10-24	1825.7
Gas Chromatography	Diketogulonic acid_TMS_16	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	standard non polar	2025-10-24	1497.46
Gas Chromatography	Diketogulonic acid_TMS_17	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2527.77
Gas Chromatography	Diketogulonic acid_TMS_18	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard non polar	2025-10-24	2079.99
Gas Chromatography	Diketogulonic acid_TMS_19	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2469.41
Gas Chromatography	Diketogulonic acid_TMS_20	C[Si](C)(C)OC[C@H](O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard non polar	2025-10-24	2477.6
Gas Chromatography	Diketogulonic acid_TMS_21	C[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2003.14
Gas Chromatography	Diketogulonic acid_TMS_22	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	2140.57
Gas Chromatography	Diketogulonic acid_TMS_23	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1569.51
Gas Chromatography	Diketogulonic acid_TMS_24	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	2358.84
Gas Chromatography	Diketogulonic acid_TMS_25	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@@H](O)CO	standard non polar	2025-10-24	2424.03
Gas Chromatography	Diketogulonic acid_TMS_26	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2010.38
Gas Chromatography	Diketogulonic acid_TMS_27	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard non polar	2025-10-24	2848.47
Gas Chromatography	Diketogulonic acid_TMS_28	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1936.38
Gas Chromatography	Diketogulonic acid_TMS_29	C[Si](C)(C)OC[C@H](O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1504.48
Gas Chromatography	Diketogulonic acid_TMS_30	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1829.99
Gas Chromatography	Diketogulonic acid_TMS_31	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2262.82
Gas Chromatography	Diketogulonic acid_TMS_1	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O	standard polar	2025-10-24	1233.0
Gas Chromatography	Diketogulonic acid_TMS_2	C[Si](C)(C)O[C@@H](CO)[C@@H](O)C(=O)C(=O)C(=O)O	standard polar	2025-10-24	2088.24
Gas Chromatography	Diketogulonic acid_TMS_3	C[Si](C)(C)O[C@@H](C(=O)C(=O)C(=O)O)[C@@H](O)CO	standard polar	2025-10-24	1886.19
Gas Chromatography	Diketogulonic acid_TMS_4	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@@H](O)CO	standard polar	2025-10-24	2254.07
Gas Chromatography	Diketogulonic acid_TMS_5	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@@H](O)CO	standard polar	2025-10-24	2609.34
Gas Chromatography	Diketogulonic acid_TMS_6	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O	standard polar	2025-10-24	2362.64
Gas Chromatography	Diketogulonic acid_TMS_7	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	standard polar	2025-10-24	2012.28
Gas Chromatography	Diketogulonic acid_TMS_8	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2260.26
Gas Chromatography	Diketogulonic acid_TMS_9	C[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard polar	2025-10-24	2252.02
Gas Chromatography	Diketogulonic acid_TMS_10	C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	standard polar	2025-10-24	2012.59
Gas Chromatography	Diketogulonic acid_TMS_11	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2114.83
Gas Chromatography	Diketogulonic acid_TMS_12	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2194.47
Gas Chromatography	Diketogulonic acid_TMS_13	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C)[C@@H](O)CO	standard polar	2025-10-24	2100.98
Gas Chromatography	Diketogulonic acid_TMS_14	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C)[C@@H](O)CO	standard polar	2025-10-24	1603.77
Gas Chromatography	Diketogulonic acid_TMS_15	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)[C@@H](O)CO	standard polar	2025-10-24	2545.16
Gas Chromatography	Diketogulonic acid_TMS_16	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	standard polar	2025-10-24	2788.98
Gas Chromatography	Diketogulonic acid_TMS_17	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1892.51
Gas Chromatography	Diketogulonic acid_TMS_18	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard polar	2025-10-24	1674.61
Gas Chromatography	Diketogulonic acid_TMS_19	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1674.71
Gas Chromatography	Diketogulonic acid_TMS_20	C[Si](C)(C)OC[C@H](O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard polar	2025-10-24	1842.66
Gas Chromatography	Diketogulonic acid_TMS_21	C[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1820.98
Gas Chromatography	Diketogulonic acid_TMS_22	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	3568.5
Gas Chromatography	Diketogulonic acid_TMS_23	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1460.27
Gas Chromatography	Diketogulonic acid_TMS_24	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1838.25
Gas Chromatography	Diketogulonic acid_TMS_25	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@@H](O)CO	standard polar	2025-10-24	1811.65
Gas Chromatography	Diketogulonic acid_TMS_26	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2127.36
Gas Chromatography	Diketogulonic acid_TMS_27	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O	standard polar	2025-10-24	2754.56
Gas Chromatography	Diketogulonic acid_TMS_28	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2854.45
Gas Chromatography	Diketogulonic acid_TMS_29	C[Si](C)(C)OC[C@H](O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1848.13
Gas Chromatography	Diketogulonic acid_TMS_30	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2637.03
Gas Chromatography	Diketogulonic acid_TMS_31	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1629.18

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	28	Pig ; Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	13	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0005971

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112185

KNApSAcK ID

Not Available

Chemspider ID

389343

KEGG Compound ID

C04575

BioCyc ID

CPD-334

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440390

PDB ID

Not Available

ChEBI ID

15622

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Karkonen A, Fry SC: Effect of ascorbate and its oxidation products on H2O2 production in cell-suspension cultures of Picea abies and in the absence of cells. J Exp Bot. 2006;57(8):1633-44. doi: 10.1093/jxb/erj197. Epub 2006 May 12. [PubMed:16698813 ]
Linster CL, Van Schaftingen E: Vitamin C. Biosynthesis, recycling and degradation in mammals. FEBS J. 2007 Jan;274(1):1-22. doi: 10.1111/j.1742-4658.2006.05607.x. [PubMed:17222174 ]

Showing metabocard for Diketogulonic acid (MMDBc0047946)

MOL for #<Metabolite:0x00007f9ab01b6028>

3D MOL for #<Metabolite:0x00007f9ab01b6028>

3D SDF for #<Metabolite:0x00007f9ab01b6028>

3D-SDF for #<Metabolite:0x00007f9ab01b6028>

PDB for #<Metabolite:0x00007f9ab01b6028>

3D PDB for #<Metabolite:0x00007f9ab01b6028>

SMILES for #<Metabolite:0x00007f9ab01b6028>

INCHI for #<Metabolite:0x00007f9ab01b6028>

Structure for #<Metabolite:0x00007f9ab01b6028>

3D Structure for #<Metabolite:0x00007f9ab01b6028>