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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 05:44:02 UTC

Update Date

2023-02-21 17:31:05 UTC

HMDB ID

HMDB0062706

Secondary Accession Numbers

HMDB62706

Metabolite Identification

Common Name

Dehydroascorbide(1-)

Description

dehydroascorbide(1-) belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. dehydroascorbide(1-) is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  O   UNK     0      -0.274   5.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5                                                       
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.108

Monoisotopic Molecular Weight

174.016437913

IUPAC Name

5-(1,2-dihydroxyethyl)-4-hydroxy-2,3-dihydrofuran-2,3-dione

Traditional Name

5-(1,2-dihydroxyethyl)-4-hydroxyfuran-2,3-dione

CAS Registry Number

Not Available

SMILES

OCC(O)C1=C(O)C(=O)C(=O)O1

InChI Identifier

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

InChI Key

JMMUPWYGEQCUML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

3-furanone
1,2-diol
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Lactone
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

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	323 g/l	ALOGPS
LogP	-0.98	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.3	ALOGPS
logP	-1.5	ChemAxon
logS	-0.04	ALOGPS
pKa (Strongest Acidic)	5.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.42 m³·mol⁻¹	ChemAxon
Polarizability	14.46 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	138.227	30932474
DeepCCS	[M-H]-	134.488	30932474
DeepCCS	[M-2H]-	171.661	30932474
DeepCCS	[M+Na]+	147.109	30932474
AllCCS	[M+H]+	136.3	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.5	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	128.9	32859911
AllCCS	[M+HCOO]-	129.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroascorbide(1-)	OCC(O)C1=C(O)C(=O)C(=O)O1	3144.8	Standard polar	33892256
Dehydroascorbide(1-)	OCC(O)C1=C(O)C(=O)C(=O)O1	1695.6	Standard non polar	33892256
Dehydroascorbide(1-)	OCC(O)C1=C(O)C(=O)C(=O)O1	1590.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroascorbide(1-),1TMS,isomer #1	C[Si](C)(C)OCC(O)C1=C(O)C(=O)C(=O)O1	1684.4	Semi standard non polar	33892256
Dehydroascorbide(1-),1TMS,isomer #2	C[Si](C)(C)OC(CO)C1=C(O)C(=O)C(=O)O1	1706.2	Semi standard non polar	33892256
Dehydroascorbide(1-),1TMS,isomer #3	C[Si](C)(C)OC1=C(C(O)CO)OC(=O)C1=O	1646.2	Semi standard non polar	33892256
Dehydroascorbide(1-),2TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C1=C(O)C(=O)C(=O)O1	1777.3	Semi standard non polar	33892256
Dehydroascorbide(1-),2TMS,isomer #2	C[Si](C)(C)OCC(O)C1=C(O[Si](C)(C)C)C(=O)C(=O)O1	1774.8	Semi standard non polar	33892256
Dehydroascorbide(1-),2TMS,isomer #3	C[Si](C)(C)OC1=C(C(CO)O[Si](C)(C)C)OC(=O)C1=O	1787.6	Semi standard non polar	33892256
Dehydroascorbide(1-),3TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(=O)C(=O)O1	1911.8	Semi standard non polar	33892256
Dehydroascorbide(1-),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O)C1=C(O)C(=O)C(=O)O1	1956.1	Semi standard non polar	33892256
Dehydroascorbide(1-),1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CO)C1=C(O)C(=O)C(=O)O1	1989.4	Semi standard non polar	33892256
Dehydroascorbide(1-),1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C(O)CO)OC(=O)C1=O	1932.3	Semi standard non polar	33892256
Dehydroascorbide(1-),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=C(O)C(=O)C(=O)O1	2300.7	Semi standard non polar	33892256
Dehydroascorbide(1-),2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O)C1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O1	2291.6	Semi standard non polar	33892256
Dehydroascorbide(1-),2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C(CO)O[Si](C)(C)C(C)(C)C)OC(=O)C1=O	2329.0	Semi standard non polar	33892256
Dehydroascorbide(1-),3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O1	2630.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroascorbide(1-) 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 - Dehydroascorbide(1-) 10V, Positive-QTOF	splash10-056r-3900000000-4a41f8bfe7584f3ea7a9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 20V, Positive-QTOF	splash10-0a6r-4900000000-474fafdde244989c3a60	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 40V, Positive-QTOF	splash10-0a4i-9000000000-f317245a12a25394a7eb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 10V, Negative-QTOF	splash10-00di-2900000000-0839cd58977040eb3832	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 20V, Negative-QTOF	splash10-0h90-3900000000-3f20debac5d93d9bea70	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 40V, Negative-QTOF	splash10-06r6-9200000000-4e2febb6b3eb27d618b9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 10V, Positive-QTOF	splash10-014i-1900000000-ee7b13245b5c61a3eebf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 20V, Positive-QTOF	splash10-0006-9200000000-f52acc895fc20a0b878d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 40V, Positive-QTOF	splash10-052f-9000000000-d538aa110fa999028138	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 10V, Negative-QTOF	splash10-03di-0900000000-1382c92f955df368fdbc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 20V, Negative-QTOF	splash10-08fr-5900000000-e0cc2952e075ef1ba19d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroascorbide(1-) 40V, Negative-QTOF	splash10-0a59-9300000000-466bb025453855f579b8	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49791982

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Dehydroascorbide(1-) (HMDB0062706)

MOL for HMDB0062706 (Dehydroascorbide(1-))

3D MOL for HMDB0062706 (Dehydroascorbide(1-))

3D SDF for HMDB0062706 (Dehydroascorbide(1-))

3D-SDF for HMDB0062706 (Dehydroascorbide(1-))

PDB for HMDB0062706 (Dehydroascorbide(1-))

3D PDB for HMDB0062706 (Dehydroascorbide(1-))

SMILES for HMDB0062706 (Dehydroascorbide(1-))

INCHI for HMDB0062706 (Dehydroascorbide(1-))

Structure for HMDB0062706 (Dehydroascorbide(1-))

3D Structure for HMDB0062706 (Dehydroascorbide(1-))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra