MiMeDB: Showing metabocard for dehydroascorbate (bicyclic form) (MMDBc0032116)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:03:04 UTC

Update Date

2022-08-31 18:30:40 UTC

Metabolite ID

MMDBc0032116

Metabolite Identification

Common Name

dehydroascorbate (bicyclic form)

Description

NULL

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    5    8                                                  
CONECT    3    4    5    9                                                  
CONECT    4    3    6   10                                                  
CONECT    5    2    3   12                                                  
CONECT    6    4   11   12                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
Dehydroascorbate	ChEBI
Dehydroascorbates	ChEBI

Molecular Formula

C₆H₆O₆

Average Mass

174.1082

Monoisotopic Mass

174.016437924

IUPAC Name

5-(1,2-dihydroxyethyl)oxolane-2,3,4-trione

Traditional Name

dehydroascorbic acid

CAS Registry Number

Not Available

SMILES

OCC(O)C1OC(=O)C(=O)C1=O

InChI Identifier

InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2

InChI Key

SBJKKFFYIZUCET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

3-furanone
Gamma butyrolactone
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

tetrahydrofuranone (CHEBI:17242 )
a small molecule (L-DEHYDRO-ASCORBATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	190 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.67	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.55 m³·mol⁻¹	ChemAxon
Polarizability	14.12 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-1900000000-9e9b54697233d78ff471	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-e7da2430489db635dea0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-decb0d5cef54ccf67907	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-1900000000-c546ba0f061c1d25a934	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0mbc-2900000000-254c596333e32143329f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fr-9700000000-c03aa7ab2f0113898ab3	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

Metabolic Reactions

Not Available

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Plant	Plant	Malus pumila	FooDB	31437929
Plant	Fruit	Hippophae rhamnoides	FooDB	31437929
Plant	Fruit	Physalis philadelphica var. immaculata	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant	Floret	Brassica oleracea var. italica	FooDB	31437929
Plant	Sprout seedling	Vigna mungo	FooDB	31437929
Plant	Seed	Pisum sativum	FooDB	31437929
Plant	Leaves	Spinacia oleracea	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Plant	Allium ampeloprasum	FooDB	31437929
Plant	Shoot	Apium graveolens	FooDB	31437929
Plant	Shoot	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Shoot	Brassica oleracea var. capitata	FooDB	31437929
Plant	Root	Manihot esculenta	FooDB	31437929
Plant	Root	Daucus carota	FooDB	31437929
Plant	Fruit	Musa x paradisiaca	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011907

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dehydroascorbic acid

METLIN ID

Not Available

PubChem Compound

835

PDB ID

Not Available

ChEBI ID

17242

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for dehydroascorbate (bicyclic form) (MMDBc0032116)

MOL for #<Metabolite:0x00007fed14bd7b40>

3D MOL for #<Metabolite:0x00007fed14bd7b40>

3D SDF for #<Metabolite:0x00007fed14bd7b40>

3D-SDF for #<Metabolite:0x00007fed14bd7b40>

PDB for #<Metabolite:0x00007fed14bd7b40>

3D PDB for #<Metabolite:0x00007fed14bd7b40>

SMILES for #<Metabolite:0x00007fed14bd7b40>

INCHI for #<Metabolite:0x00007fed14bd7b40>

Structure for #<Metabolite:0x00007fed14bd7b40>

3D Structure for #<Metabolite:0x00007fed14bd7b40>