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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:00 -0600
Update Date	2015-09-08 17:50:00 -0600
Secondary Accession Numbers	ECMDB24193
Identification
Name:	dehydroascorbate (bicyclic form)
Description
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x4d96ddc> Close
Synonyms:	Dehydroascorbic acid (bicyclic form)
Chemical Formula:	C6H6O6
Weight:	Average: 174.1082 Monoisotopic: 174.016437924
InChI Key:	SBJKKFFYIZUCET-UHFFFAOYSA-N
InChI:	InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2
CAS number:	Not Available
IUPAC Name:	(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
Traditional IUPAC Name:	(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
SMILES:	OCC(O)C1OC(=O)C(=O)C1=O
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	Furanones Tetrahydrofurans Secondary alcohols Cyclic ketones Carboxylic acid esters 1,2-diols Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives
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
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
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 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 33.55 m³·mol⁻¹ ChemAxon Polarizability 14.02 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Ascorbate metabolism PW000793
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001i-9200000000-0a414c4d59046ece51c1 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-0fki-9831000000-c4b46024e1624e983ac3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-004i-4900000000-25a652482451303b3ca4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-056r-1900000000-f1d23791c8a7b59576a3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4r-2900000000-5ebc67e43b07167f34cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0abc-9000000000-27ae8f5e1795d4f732a8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0229-0900000000-ee719ada45193fc650a0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0mbc-1900000000-d54b8e72e08e6ea1f7c0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0btc-9200000000-d07ff0053ddc28ce1915 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17242 HMDB ID HMDB0001264 Pubchem Compound ID 210328 Kegg ID C00425 ChemSpider ID 182283 Wikipedia ID Dehydroascorbic acid BioCyc ID Not Available