MiMeDB: Showing metabocard for 2,3-Diketo-L-gulonate (MMDBc0029836)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:39 UTC

Update Date

2022-08-31 17:19:13 UTC

Metabolite ID

MMDBc0029836

Metabolite Identification

Common Name

2,3-Diketo-L-gulonate

Description

2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-).

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.985 -13.161   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.651 -13.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.318 -13.161   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.984 -13.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.650 -13.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.316 -13.931   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.983 -13.161   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      22.319 -13.931   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      20.985 -11.621   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      19.651 -15.471   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      18.318 -11.621   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      16.984 -15.471   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      15.650 -11.621   0.000  0.00  0.00           O+0
CONECT    1    2    8    9                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
2,3-Diketo-L-gulonic acid	Generator
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoate	HMDB
(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid	HMDB
2,3-diketo-L Gulonic acid	HMDB
2,3-Diketogulonic acid	HMDB
Diketogulonic acid	HMDB
L-threo-2,3-Hexodiulosonic acid	HMDB
L-threo-hexo-2,3-Diulosonic acid	HMDB

Molecular Formula

C₆H₈O₇

Average Mass

192.1235

Monoisotopic Mass

192.02700261

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H](O)C(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-SCQFTWEKSA-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

Not Available

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	15.77 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 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	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-11ou-9500000000-f51f8802520502229315	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btd-9000000000-b607173f6a4870d24b5f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005j-7900000000-095b22b39dbcc6d9fa05	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-05380c64aede8d94e31b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-84c78a8bd0634d2dfffc	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000623	Dehydroascorbic acid	2,3-Diketo-L-gulonate	Not Available	VMH; KEGG	9296457
MMDBr0000788	2,3-Diketo-L-gulonate	L-Lyxonate	Not Available	VMH	9296457
MMDBr0000789	2,3-Diketo-L-gulonate	L-Xylonic acid	Not Available	VMH	9296457
MMDBr0000790	2,3-Diketo-L-gulonate	Oxalic acid	Not Available	VMH	10727845 9296457
MMDBr0000791	2,3-Diketo-L-gulonate	L-Erythrulose	Not Available	VMH	10727845
MMDBr0007678	3-Dehydro-L-gulonate	2,3-Diketo-L-gulonate	Not Available	VMH	30371894
MMDBr0007753	2,3-Diketo-L-gulonate	3-Dehydro-L-gulonate	Not Available	VMH	30371894

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	Proteobacteria	64	Pig ; Human feces; Human ; Human feces; pleural fluid plaque; bal; Human stool; Human subgingival plaque; Chicken	Unknown; Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	13	Human feces	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0006511

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023950

KNApSAcK ID

Not Available

Chemspider ID

35015997

KEGG Compound ID

C04575

BioCyc ID

Not Available

BiGG ID

45750

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477844

PDB ID

Not Available

ChEBI ID

15622

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Banhegyi G, Braun L, Csala M, Puskas F, Mandl J: Ascorbate metabolism and its regulation in animals. Free Radic Biol Med. 1997;23(5):793-803. doi: 10.1016/s0891-5849(97)00062-2. [PubMed:9296457 ]
Simpson GL, Ortwerth BJ: The non-oxidative degradation of ascorbic acid at physiological conditions. Biochim Biophys Acta. 2000 Apr 15;1501(1):12-24. doi: 10.1016/s0925-4439(00)00009-0. [PubMed:10727845 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2,3-Diketo-L-gulonate (MMDBc0029836)

MOL for #<Metabolite:0x00007fdb452e6b98>

3D MOL for #<Metabolite:0x00007fdb452e6b98>

3D SDF for #<Metabolite:0x00007fdb452e6b98>

3D-SDF for #<Metabolite:0x00007fdb452e6b98>

PDB for #<Metabolite:0x00007fdb452e6b98>

3D PDB for #<Metabolite:0x00007fdb452e6b98>

SMILES for #<Metabolite:0x00007fdb452e6b98>

INCHI for #<Metabolite:0x00007fdb452e6b98>

Structure for #<Metabolite:0x00007fdb452e6b98>

3D Structure for #<Metabolite:0x00007fdb452e6b98>