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Showing metabocard for Ascorbic acid (BMDB0000044)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:18:54 UTC
Update Date2020-06-04 20:51:07 UTC
MCDB ID BMDB0000044
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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Acide ascorbiqueChEBI
Acido ascorbicoChEBI
Acidum ascorbicumChEBI
Acidum ascorbinicumChEBI
AscoltinChEBI
AscorbicapChEBI
AscorbinsaeureChEBI
e 300ChEBI
e-300ChEBI
e300ChEBI
L-(+)-Ascorbic acidChEBI
L-AscorbateChEBI
Vitamin CChEBI
Monodehydroascorbate radicalKegg
Ascorbate radicalKegg
Semidehydroascorbic acidKegg
ASCORKegg
L-(+)-AscorbateGenerator
L-Ascorbic acidGenerator
Monodehydroascorbic acid radicalGenerator
Ascorbic acid radicalGenerator
SemidehydroascorbateGenerator
AscorbateGenerator
(+)-AscorbateHMDB
(+)-Ascorbic acidHMDB
(+)-Sodium L-ascorbateHMDB
3-keto-L-GulofuranolactoneHMDB
3-oxo-L-GulofuranolactoneHMDB
AdenexHMDB
AllercorbHMDB
Antiscorbic vitaminHMDB
Antiscorbutic vitaminHMDB
arco-CeeHMDB
Ascor-b.i.d.HMDB
AscorbHMDB
AscorbajenHMDB
AscorbicabHMDB
AscorbicinHMDB
AscorbinHMDB
AscorbutinaHMDB
AscorinHMDB
AscortealHMDB
AscorvitHMDB
C-LevelHMDB
C-LongHMDB
C-QuinHMDB
C-SpanHMDB
C-ViminHMDB
CantanHMDB
CantaxinHMDB
Catavin CHMDB
Ce lentHMDB
Ce-mi-linHMDB
Ce-vi-solHMDB
CebicureHMDB
CebidHMDB
CebionHMDB
CebioneHMDB
CeconHMDB
Cee-caps TDHMDB
Cee-viteHMDB
CegiolanHMDB
CeglionHMDB
CeklinHMDB
CelaskonHMDB
CelinHMDB
Cell CHMDB
CemagylHMDB
CemillHMDB
CenetoneHMDB
CenolateHMDB
CereonHMDB
CergonaHMDB
CescorbatHMDB
CetamidHMDB
CetaneHMDB
Cetane-caps TCHMDB
Cetane-caps TDHMDB
CetebeHMDB
CetemicanHMDB
CevalinHMDB
CevatineHMDB
CevexHMDB
Cevi-bidHMDB
CeviminHMDB
CevitalHMDB
CevitamateHMDB
Cevitamic acidHMDB
CevitaminHMDB
CevitanHMDB
CevitexHMDB
CewinHMDB
ChewceeHMDB
CiaminHMDB
CipcaHMDB
CitriscorbHMDB
CitrovitHMDB
ColascorHMDB
ConceminHMDB
Davitamon CHMDB
Dora-C-500HMDB
DuoscorbHMDB
Ferrous ascorbateHMDB, MeSH
gamma-Lactone L-threo-hex-2-enonateHMDB
gamma-Lactone L-threo-hex-2-enonic acidHMDB
HiCeeHMDB
HybrinHMDB, MeSH
ido-CHMDB
JuvamineHMDB
KangbingfengHMDB
Kyselina askorbovaHMDB
L(+)-AscorbateHMDB
L(+)-Ascorbic acidHMDB
L-3-Ketothreohexuronic acid lactoneHMDB
L-LyxoascorbateHMDB
L-Lyxoascorbic acidHMDB
L-threo-Ascorbic acidHMDB
L-XyloascorbateHMDB
L-Xyloascorbic acidHMDB
LaroscorbineHMDB
LemascorbHMDB
Liqui-ceeHMDB
Meri-cHMDB
NatrascorbHMDB
Natrascorb injectableHMDB
Planavit CHMDB
ProscorbinHMDB
RedoxonHMDB
RibenaHMDB
Ronotec 100HMDB
Rontex 100HMDB
RoscorbicHMDB
Rovimix CHMDB
ScorbacidHMDB
Scorbu CHMDB
Scorbu-CHMDB
SecorbateHMDB
SodascorbateHMDB
Suncoat VC 40HMDB
TestascorbicHMDB
VASCHMDB
VicelatHMDB
VicinHMDB
Vicomin CHMDB
ViforcitHMDB
ViscorinHMDB
Viscorin 100mHMDB
VitaceHMDB
VitaceeHMDB
VitaciminHMDB
VitacinHMDB
VitamisinHMDB
VitascorbolHMDB
XitixHMDB
L Ascorbic acidMeSH, HMDB
Acid, ascorbicMeSH, HMDB
Ascorbate, ferrousMeSH, HMDB
Ascorbate, sodiumMeSH, HMDB
Magnesium ascorbateMeSH, HMDB
Magnesium ascorbicumMeSH, HMDB
Magnesium di-L-ascorbateMeSH, HMDB
Di-L-ascorbate, magnesiumMeSH, HMDB
Ascorbic acid, monosodium saltMeSH, HMDB
Magnesium di L ascorbateMeSH, HMDB
MagnorbinMeSH, HMDB
Sodium ascorbateMeSH, HMDB
Acid, L-ascorbicMeSH, HMDB
Ascorbate, magnesiumMeSH, HMDB
ASCORBIC ACIDChEBI
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified22.71 +/- 1.42 uM details
Detected and Quantified34 +/- 1.7 uM details
Detected and Quantified153 uM
  • Int. Dairy Journa...
 details
Detected and Quantified51 uM details
Detected and Quantified51 uM details
Detected and Quantified57 uM details
Detected and Quantified51 uM details
Detected and Quantified68 uM details
Detected and Quantified57 uM details
Detected and Quantified63 uM details
Detected and Quantified57 uM details
Detected and Quantified74 uM details
Detected and Quantified74 uM details
Detected and Quantified85 uM details
Detected and Quantified63 uM details
Detected and Quantified57 uM details
Detected and Quantified63 uM details
Detected and Quantified11 uM details
Detected and Quantified11 uM details
Detected and Quantified74 uM details
Detected and Quantified74 uM details
Detected and Quantified74 uM details
Detected and Quantified68 uM details
Detected and Quantified68 uM details
Detected and Quantified68 uM details
Detected and Quantified53 uM
  • Park, Y. W; Juáre...
 details
Detected and Quantified53 - 56 uM details
Detected and Quantified62 - 129 uM details
Detected and Quantified34.7 +/- 0.2 uM details
Detected and Quantified39 +/- 1 uM details
Detected and Quantified34.0 +/- 0.3 uM details
Detected and Quantified8.2 +/- 0.3 uM details
HMDB IDHMDB0014273
DrugBank IDDB00126
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001224
KNApSAcK IDC00001179
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)Download (PDF)
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]