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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 19:03:31 UTC

Update Date

2023-02-21 17:17:10 UTC

HMDB ID

HMDB0005971

Secondary Accession Numbers

HMDB05971

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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₆H₈O₇

Average Molecular Weight

192.1235

Monoisotopic Molecular Weight

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 )

Ontology

Not Available

Endogenous (HMDB: HMDB0005971)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.19	31661259
DarkChem	[M-H]-	138.291	31661259
DeepCCS	[M+H]+	142.966	30932474
DeepCCS	[M-H]-	140.571	30932474
DeepCCS	[M-2H]-	173.733	30932474
DeepCCS	[M+Na]+	148.891	30932474
AllCCS	[M+H]+	141.1	32859911
AllCCS	[M+H-H2O]+	137.3	32859911
AllCCS	[M+NH4]+	144.6	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	134.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diketogulonic acid	OC[C@H](O)[C@@H](O)C(=O)C(=O)C(O)=O	2787.6	Standard polar	33892256
Diketogulonic acid	OC[C@H](O)[C@@H](O)C(=O)C(=O)C(O)=O	1760.0	Standard non polar	33892256
Diketogulonic acid	OC[C@H](O)[C@@H](O)C(=O)C(=O)C(O)=O	1545.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diketogulonic acid,1TMS,isomer #1	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O	1645.5	Semi standard non polar	33892256
Diketogulonic acid,1TMS,isomer #2	C[Si](C)(C)O[C@@H](CO)[C@@H](O)C(=O)C(=O)C(=O)O	1669.8	Semi standard non polar	33892256
Diketogulonic acid,1TMS,isomer #3	C[Si](C)(C)O[C@@H](C(=O)C(=O)C(=O)O)[C@@H](O)CO	1643.5	Semi standard non polar	33892256
Diketogulonic acid,1TMS,isomer #4	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@@H](O)CO	1642.7	Semi standard non polar	33892256
Diketogulonic acid,1TMS,isomer #5	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@@H](O)CO	1681.9	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O	1756.6	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)[C@@H](O)CO	1725.6	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #2	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	1750.1	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #3	C[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C	1750.4	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #4	C[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C)C(=O)C(=O)O	1744.6	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #5	C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)C(=O)C(=O)C(=O)O	1758.2	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@H](CO)O[Si](C)(C)C	1765.2	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #7	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@H](CO)O[Si](C)(C)C	1765.4	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #8	C[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C)[C@@H](O)CO	1742.0	Semi standard non polar	33892256
Diketogulonic acid,2TMS,isomer #9	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C)[C@@H](O)CO	1748.3	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #1	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	1836.7	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)[C@@H](O)CO	1816.3	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #2	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	1846.4	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #3	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	1830.1	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #4	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	1851.9	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #5	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	1846.6	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #6	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	1809.3	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #7	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	1847.7	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #8	C[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1862.2	Semi standard non polar	33892256
Diketogulonic acid,3TMS,isomer #9	C[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C)=C(O)[C@H](CO)O[Si](C)(C)C	1819.3	Semi standard non polar	33892256
Diketogulonic acid,4TMS,isomer #1	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	1896.3	Semi standard non polar	33892256
Diketogulonic acid,4TMS,isomer #2	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	1916.6	Semi standard non polar	33892256
Diketogulonic acid,4TMS,isomer #3	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	1861.8	Semi standard non polar	33892256
Diketogulonic acid,4TMS,isomer #4	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	1894.9	Semi standard non polar	33892256
Diketogulonic acid,4TMS,isomer #5	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	1907.3	Semi standard non polar	33892256
Diketogulonic acid,5TMS,isomer #1	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	1890.0	Semi standard non polar	33892256
Diketogulonic acid,5TMS,isomer #1	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	1919.8	Standard non polar	33892256
Diketogulonic acid,5TMS,isomer #1	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	1949.7	Standard polar	33892256
Diketogulonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O	1901.4	Semi standard non polar	33892256
Diketogulonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O)C(=O)C(=O)C(=O)O	1926.1	Semi standard non polar	33892256
Diketogulonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H](C(=O)C(=O)C(=O)O)[C@@H](O)CO	1909.3	Semi standard non polar	33892256
Diketogulonic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@@H](O)CO	1891.7	Semi standard non polar	33892256
Diketogulonic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@@H](O)CO	1958.9	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O	2226.6	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O)[C@@H](O)CO	2214.2	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)C(=O)C(=O)O	2224.5	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2197.5	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O	2220.7	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)C(=O)C(=O)O	2221.0	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O)[C@H](CO)O[Si](C)(C)C(C)(C)C	2227.0	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(C(=O)C(=O)O)=C(O)[C@H](CO)O[Si](C)(C)C(C)(C)C	2252.0	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	2211.1	Semi standard non polar	33892256
Diketogulonic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	2244.6	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)C(=O)C(=O)O	2508.5	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	2517.5	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2504.4	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O	2502.8	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2535.7	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H](O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O	2545.3	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@H](O)C(O)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2493.5	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2530.0	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(C(=O)C(=O)O)=C(O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2550.1	Semi standard non polar	33892256
Diketogulonic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O)[C@H](CO)O[Si](C)(C)C(C)(C)C	2508.0	Semi standard non polar	33892256
Diketogulonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2755.1	Semi standard non polar	33892256
Diketogulonic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O	2759.2	Semi standard non polar	33892256
Diketogulonic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2727.1	Semi standard non polar	33892256
Diketogulonic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2762.1	Semi standard non polar	33892256
Diketogulonic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C(=O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2770.8	Semi standard non polar	33892256
Diketogulonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2972.2	Semi standard non polar	33892256
Diketogulonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2800.9	Standard non polar	33892256
Diketogulonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C	2570.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diketogulonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nn9-9200000000-1cbed9b2b56caa085c4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diketogulonic acid GC-MS (4 TMS) - 70eV, Positive	splash10-02or-7339800000-1615efb2d0feaa5735ea	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diketogulonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diketogulonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 10V, Positive-QTOF	splash10-004l-1900000000-1d6c68c73855ddcddb54	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 20V, Positive-QTOF	splash10-08mi-9500000000-c792fe4653b44e9ab372	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 40V, Positive-QTOF	splash10-0ab9-9000000000-16a4d7310299656e7744	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 10V, Negative-QTOF	splash10-0g4l-9700000000-6d882e161ed0ab1a7656	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 20V, Negative-QTOF	splash10-0a4r-9300000000-c5167767732d60eead4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-f6c0690482bc1a940237	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 10V, Positive-QTOF	splash10-01c0-6900000000-f68a48e03dbb51e87373	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 20V, Positive-QTOF	splash10-11ou-9500000000-f51f8802520502229315	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 40V, Positive-QTOF	splash10-0btd-9000000000-b607173f6a4870d24b5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 10V, Negative-QTOF	splash10-005j-7900000000-095b22b39dbcc6d9fa05	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 20V, Negative-QTOF	splash10-0pb9-9200000000-05380c64aede8d94e31b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diketogulonic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-84c78a8bd0634d2dfffc	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Linster CL, Van Schaftingen E: Vitamin C. Biosynthesis, recycling and degradation in mammals. FEBS J. 2007 Jan;274(1):1-22. [PubMed:17222174 ]
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. Epub 2006 May 12. [PubMed:16698813 ]

Showing metabocard for Diketogulonic acid (HMDB0005971)

MOL for HMDB0005971 (Diketogulonic acid)

3D MOL for HMDB0005971 (Diketogulonic acid)

3D SDF for HMDB0005971 (Diketogulonic acid)

3D-SDF for HMDB0005971 (Diketogulonic acid)

PDB for HMDB0005971 (Diketogulonic acid)

3D PDB for HMDB0005971 (Diketogulonic acid)

SMILES for HMDB0005971 (Diketogulonic acid)

INCHI for HMDB0005971 (Diketogulonic acid)

Structure for HMDB0005971 (Diketogulonic acid)

3D Structure for HMDB0005971 (Diketogulonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra