Showing metabocard for Ascorbic acid (BMDB0000044)

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Record Information
Version1.0
Creation Date2016-09-30 22:18:54 UTC
Update Date2020-06-04 20:51:07 UTC
BMDB IDBMDB0000044
Secondary Accession Numbers
  • BMDB00044
  • BMDB0014273
  • BMDB14273
Metabolite Identification
Common NameAscorbic acid
DescriptionAscorbic acid, also known as ascorbate, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Ascorbic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dopamine and ascorbic acid can be converted into norepinephrine and dehydroascorbic acid through the action of the enzyme dopamine beta-hydroxylase. In cattle, ascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Chemical FormulaC6H8O6
Average Molecular Weight176.1241
Monoisotopic Molecular Weight176.032087988
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional Namevitamin C
CAS Registry NumberNot Available
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
InChI KeyCIWBSHSKHKDKBQ-JLAZNSOCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.03 m³·mol⁻¹ChemAxon
Polarizability14.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e99089fd55560fb70cfeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0912000000-baa8cffda0478e1bc197View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-c1dc72c6cbc49fbf3454View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-b207f4024993c5a74769View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-9af0c08e85e0c51a25c4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e99089fd55560fb70cfeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0912000000-baa8cffda0478e1bc197View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-c1dc72c6cbc49fbf3454View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-b207f4024993c5a74769View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-9af0c08e85e0c51a25c4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-9700000000-ab53eee999ee7fee672dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0kkj-9357500000-5c2c439f726b729dd50dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0002-9300000000-d8c8254ad1dd4de2674cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-004i-1900000000-da5bc92501d37735007fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0006-0900000000-b653774b8718c29fe97aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-9200000000-5d1ea04ef6404f5ecf7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-000i-9000000000-0371d7191fa8a89176f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, negativesplash10-004i-0900000000-76825c62319d5f4cbed9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, negativesplash10-016r-2900000000-700d5d6247efb36c48d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, negativesplash10-014i-8900000000-4d76fc951d56a75a025eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, negativesplash10-05tr-9300000000-0967cf71e141f71c2e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-052r-9100000000-2bca6a943255612f1e7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-9000000000-804b40cc657a43d298fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0a4i-9000000000-cad0cc415c906a783cfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0a4r-9000000000-f79a7dfc866621b3c926View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-707796161cd4fae98f67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-035a78987127cc9f23f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-dac785ef05051971e946View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00or-1900000000-a91dc1a29cb724a17811View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-016r-3900000000-78f1f46067d2459f17c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-014i-6900000000-8044f242bb90f54a595aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kdi-2900000000-f05a720e6e6361c97e5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-5900000000-6ca3f37a74403d8495c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-5625440c512f60760fdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0o90-2900000000-b7c897849334927f5bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-4900000000-1f1fa10e7e06a79c028aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9300000000-b98375c0cd3a54b61ef7View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Medulla
  • Bladder
  • Blood
  • Brain
  • Epidermis
  • Erythrocyte
  • Eye Lens
  • Fibroblasts
  • Heart
  • Intestine
  • Leukocyte
  • Liver
  • Lung
  • Mammary Gland
  • Milk
  • Neuron
  • Ovary
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0014273
DrugBank IDDB00126
Phenol Explorer Compound IDNot Available
FooDB IDFDB001224
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01041
BioCyc IDASCORBATE
BiGG IDNot Available
Wikipedia LinkAscorbic_Acid
METLIN IDNot Available
PubChem Compound54670067
PDB IDNot Available
ChEBI ID29073
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74. [PubMed:1880195 ]
  2. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
  3. Weiss WP, Hogan JS, Smith KL: Changes in vitamin C concentrations in plasma and milk from dairy cows after an intramammary infusion of Escherichia coli. J Dairy Sci. 2004 Jan;87(1):32-7. doi: 10.3168/jds.S0022-0302(04)73138-0. [PubMed:14765807 ]
  4. Ingela Andersson, R. Öste (1994). Int. Dairy Journal 4 (1994) 161-172. International Dairy Journal.
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  6. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  7. USDA Food Composition Databases [Link]
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details
1. Dopamine beta-hydroxylase
General function:
Involved in copper ion binding
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P15101
Molecular weight:
68141.0
Reactions
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Waterdetails