L-ascorbate (PAMDB120038)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120038
Identification
Name: L-ascorbate
Description:The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Ascorbate
  • L-Ascorbate
  • L-ascorbate
  • L-ascorbate(1−)
  • L-ascorbic acid, ion(1−)
  • Vitamin C
Chemical Formula: C6H7O6
Average Molecular Weight: 175.118
Monoisotopic Molecular Weight: 176.03209
InChI Key: CIWBSHSKHKDKBQ-SZSCBOSDSA-M
InChI:InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/p-1/t2-,5?/m0/s1
CAS number: 50-81-7
IUPAC Name:(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate
Traditional IUPAC Name: vitamin C
SMILES:C(O)C(O)C1(C([O-])=C(O)C(=O)O1)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Dihydrofurans
Sub ClassFuranones
Direct Parent Butenolides
Alternative Parents
Substituents
  • 2-furanone
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Carboxylic acid ester
  • Enediol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 191 °C [PhysProp]
Experimental Properties:
PropertyValueReference
Melting Point191 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility400 mg/mL at 40 °CMERCK INDEX (1996)
LogP-1.85AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
Water Solubility245.0 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.9ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.03 m3·mol-1ChemAxon
Polarizability14.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
L-sorbosone 1,4-lactone + Acceptor → L-ascorbate + Donor-H2 + Hydrogen ion
monodehydroascorbate radical → L-ascorbate + L-dehydro-ascorbate + Hydrogen ion
L-ascorbate + Hydrogen peroxide + Hydrogen ion → monodehydroascorbate radical + Water
L-ascorbate → L-dehydro-ascorbate + Hydrogen ion
Acceptor + L-ascorbate + Hydrogen ion → Donor-H2 + monodehydroascorbate radical
L-ascorbate + Hydrogen peroxide + Hydrogen ion → L-ascorbate + L-dehydro-ascorbate + Water
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • Duconge J, Miranda-Massari JR, Gonzalez MJ, Jackson JA, Warnock W, Riordan NH (2008)Pharmacokinetics of vitamin C: insights into the oral and intravenous administration of ascorbate. Puerto Rico health sciences journal 27, Pubmed: 18450228
  • Shamsi FA, Partal A, Sady C, Glomb MA, Nagaraj RH (1998)Immunological evidence for methylglyoxal-derived modifications in vivo. Determination of antigenic epitopes. The Journal of biological chemistry 273, Pubmed: 9506998
  • Chen Q, Espey MG, Sun AY, Pooput C, Kirk KL, Krishna MC, Khosh DB, Drisko J, Levine M (2008)Pharmacologic doses of ascorbate act as a prooxidant and decrease growth of aggressive tumor xenografts in mice. Proceedings of the National Academy of Sciences of the United States of America 105, Pubmed: 18678913
  • Harrison FE, May JM (2009)Vitamin C function in the brain: vital role of the ascorbate transporter SVCT2. Free radical biology & medicine 46, Pubmed: 19162177
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC38290
HMDBHMDB00044
BIGG33747
CHEMSPIDER102746
PUBCHEM54679076
CHEBI38290
KNAPSACKC00001179
LIGAND-CPDC00072
CAS50-81-7