MiMeDB: Showing metabocard for Dehydroascorbic acid (MMDBc0031994)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:53 UTC

Update Date

2022-12-15 22:51:50 UTC

Metabolite ID

MMDBc0031994

Metabolite Identification

Common Name

Dehydroascorbic acid

Description

NULL

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023512D          

 14 14  0  0  1  0            999 V2000
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    1.5268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  1  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  2  8  1  1  0  0  0
  9  3  2  0  0  0  0
 10  4  2  0  0  0  0
 11  6  2  0  0  0  0
 12  5  1  0  0  0  0
 12  6  1  0  0  0  0
  2 13  1  1  0  0  0
  5 14  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031994

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CO)[C@@]1([H])OC(=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/t2-,5-/m1/s1

> <INCHI_KEY>
SBJKKFFYIZUCET-DUZGATOHSA-N

> <FORMULA>
C6H6O6

> <MOLECULAR_WEIGHT>
174.1082

> <EXACT_MASS>
174.016437924

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.019970346878242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

> <ALOGPS_LOGP>
-1.17

> <JCHEM_LOGP>
-0.6728306333333334

> <ALOGPS_LOGS>
0.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.947507235055642

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5571896779025947

> <JCHEM_PKA_STRONGEST_BASIC>
-2.980802852202162

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
33.5458

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       2.393   2.850   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.312   2.779   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    5    8   13                                             
CONECT    3    4    5    9                                                  
CONECT    4    3    6   10                                                  
CONECT    5    2    3   12   14                                             
CONECT    6    4   11   12                                                  
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    5    6                                                       
CONECT   13    2                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
Dehydroascorbate	Generator
1-Dehydroascorbate	HMDB
1-Dehydroascorbic acid	HMDB
Dehydro-L-ascorbate	HMDB
Dehydro-L-ascorbic acid	HMDB
DHAA	HMDB
L-Dehydroascorbate	HMDB
L-Dehydroascorbic acid	HMDB
L-Threo-2,3-hexodiulosonic acid gamma-lactone	HMDB
L-Threo-hexo-2,3-diulosono-1,4-lactone	HMDB
Oxidized ascorbate	HMDB
Oxidized ascorbic acid	HMDB
Oxidized vitamin C	HMDB
Dehydroerythorbic acid	HMDB

Molecular Formula

C₆H₆O₆

Average Mass

174.1082

Monoisotopic Mass

174.016437924

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CO)[C@@]1([H])OC(=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/t2-,5-/m1/s1

InChI Key

SBJKKFFYIZUCET-DUZGATOHSA-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

Not Available

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	14.02 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 (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-0a414c4d59046ece51c1	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fki-9831000000-c4b46024e1624e983ac3	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-4900000000-25a652482451303b3ca4	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-1900000000-f1d23791c8a7b59576a3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-2900000000-5ebc67e43b07167f34cb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-9000000000-27ae8f5e1795d4f732a8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-0900000000-ee719ada45193fc650a0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0mbc-1900000000-d54b8e72e08e6ea1f7c0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9200000000-d07ff0053ddc28ce1915	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Brain
Erythrocyte
Feces
Intestine
Placenta
Platelet

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
MMDBr0000335	Ascorbic acid	Dehydroascorbic acid	Not Available	VMH	30371894
MMDBr0000623	Dehydroascorbic acid	2,3-Diketo-L-gulonate	Not Available	VMH; KEGG	9296457
MMDBr0000624	Dehydroascorbic acid	Ascorbic acid	glutaredoxin (thioltransferase)	VMH	11297543
MMDBr0000810	Ascorbic acid	Dehydroascorbic acid	dopamine beta-hydroxylase (dopamine beta-monooxygenase)	VMH	30371894
MMDBr0001214	Ascorbic acid	Dehydroascorbic acid	cytochrome b reductase 1	VMH	11230685 12755454
MMDBr0001381	Dehydroascorbic acid	Ascorbic acid	Not Available	VMH	15970797 16399380
MMDBr0004368	Ascorbic acid	7-Hydroxy-E4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004369	Ascorbic acid	7-Hydroxy-D4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004370	Ascorbic acid	11-Hydroxy-E4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004371	Ascorbic acid	11-Hydroxy-D4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004372	Ascorbic acid	10-Hydroxy-E4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004373	Ascorbic acid	10-Hydroxy-D4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004374	Ascorbic acid	14-Hydroxy-E4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004375	Ascorbic acid	14-Hydroxy-D4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004376	Ascorbic acid	13-Hydroxy-E4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004380	Ascorbic acid	20-Hydroxy-D4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004381	Ascorbic acid	20-Hydroxy-E4-Neuroprostane	Not Available	VMH	10694406 12088281
MMDBr0004386	Monodehydroascorbate	Dehydroascorbic acid	Not Available	VMH	11160563
MMDBr0004387	Dihydrolipoate	Ascorbic acid	Not Available	VMH	11160563
MMDBr0004815	Ascorbic acid	5,9,11-Trihydroxyprosta-6E,14Z-Dien-1-Oate	Not Available	VMH	2123555
MMDBr0004821	Ascorbic acid	5,9-Cyclo-6,8,12-Trihydroxy-(10E,14Z)-Eicosadienoic Acid	Not Available	VMH	2123555

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

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Blood	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001264

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021459

KNApSAcK ID

Not Available

Chemspider ID

182283

KEGG Compound ID

C00425

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17242

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Morrow JD, Hill KE, Burk RF, Nammour TM, Badr KF, Roberts LJ 2nd: A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc Natl Acad Sci U S A. 1990 Dec;87(23):9383-7. doi: 10.1073/pnas.87.23.9383. [PubMed:2123555 ]
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 ]
Packer L, Weber SU, Rimbach G: Molecular aspects of alpha-tocotrienol antioxidant action and cell signalling. J Nutr. 2001 Feb;131(2):369S-73S. doi: 10.1093/jn/131.2.369S. [PubMed:11160563 ]
Lundberg M, Johansson C, Chandra J, Enoksson M, Jacobsson G, Ljung J, Johansson M, Holmgren A: Cloning and expression of a novel human glutaredoxin (Grx2) with mitochondrial and nuclear isoforms. J Biol Chem. 2001 Jul 13;276(28):26269-75. doi: 10.1074/jbc.M011605200. Epub 2001 Apr 10. [PubMed:11297543 ]
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 ]

Showing metabocard for Dehydroascorbic acid (MMDBc0031994)

MOL for #<Metabolite:0x00007fdb02697820>

3D MOL for #<Metabolite:0x00007fdb02697820>

3D SDF for #<Metabolite:0x00007fdb02697820>

3D-SDF for #<Metabolite:0x00007fdb02697820>

PDB for #<Metabolite:0x00007fdb02697820>

3D PDB for #<Metabolite:0x00007fdb02697820>

SMILES for #<Metabolite:0x00007fdb02697820>

INCHI for #<Metabolite:0x00007fdb02697820>

Structure for #<Metabolite:0x00007fdb02697820>

3D Structure for #<Metabolite:0x00007fdb02697820>