You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:40:32 UTC
Update Date2016-09-23 18:44:28 UTC
LmdbLMDB00016
Secondary Accession NumbersNone
Metabolite Identification
Common NameAscorbic acid
DescriptionAscorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in animal diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including animals) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. [PubChem] Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants. (PMID: 10799361 ).
Structure
Thumb
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 Number50-81-7
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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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 KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e99089fd55560fb70cfeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0912000000-baa8cffda0478e1bc197Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-c1dc72c6cbc49fbf3454Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-b207f4024993c5a74769Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-9af0c08e85e0c51a25c4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e99089fd55560fb70cfeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0912000000-baa8cffda0478e1bc197Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-c1dc72c6cbc49fbf3454Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9400000000-b207f4024993c5a74769Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-9af0c08e85e0c51a25c4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-9700000000-ab53eee999ee7fee672dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0kkj-9357500000-5c2c439f726b729dd50dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0002-9300000000-d8c8254ad1dd4de2674cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-004i-1900000000-da5bc92501d37735007fSpectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-0006-0900000000-b653774b8718c29fe97aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-9200000000-5d1ea04ef6404f5ecf7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-000i-9000000000-0371d7191fa8a89176f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, negativesplash10-004i-0900000000-76825c62319d5f4cbed9Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, negativesplash10-016r-2900000000-700d5d6247efb36c48d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, negativesplash10-014i-8900000000-4d76fc951d56a75a025eSpectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, negativesplash10-05tr-9300000000-0967cf71e141f71c2e00Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-052r-9100000000-2bca6a943255612f1e7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-9000000000-804b40cc657a43d298fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0a4i-9000000000-cad0cc415c906a783cfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-0a4r-9000000000-f79a7dfc866621b3c926Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-707796161cd4fae98f67Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-035a78987127cc9f23f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-0900000000-dac785ef05051971e946Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00or-1900000000-a91dc1a29cb724a17811Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-016r-3900000000-78f1f46067d2459f17c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-014i-6900000000-8044f242bb90f54a595aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kdi-2900000000-f05a720e6e6361c97e5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-5900000000-6ca3f37a74403d8495c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-5625440c512f60760fdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0o90-2900000000-b7c897849334927f5bf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-4900000000-1f1fa10e7e06a79c028aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9300000000-b98375c0cd3a54b61ef7Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Liver
  • Lung
  • Milk
  • Vitreous Humour
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LungDetected and Quantified0.44+/-0.04 umol/gNot AvailablePorcine details
MilkDetected and Quantified12.9 mg/kgNot AvailableCaprine
    • Park, Y. W; Juáre...
details
Vitreous HumourDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDDB00126
HMDB IDHMDB0014273
FooDB IDFDB001224
Phenol Explorer IDNot Available
KNApSAcK IDC00001179
BiGG IDNot Available
BioCyc IDASCORBATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAscorbic_Acid
Chemspider ID10189562
ChEBI ID29073
PubChem Compound IDNot Available
Kegg Compound IDC01041
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Padayatty SJ, Levine M: Vitamin C and myocardial infarction: the heart of the matter. Am J Clin Nutr. 2000 May;71(5):1027-8. [10799361 ]