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Bovine Metabolome Database



Showing metabocard for Ascorbic acid (BMDB00044)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:39
Accession Number BMDB00044
Common Name Ascorbic acid
Description Ascorbic acid is an essential nutrient in human diets, and 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 humans) 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. 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)
Synonyms
  1. (+)-ascorbate
  2. (+)-ascorbic acid
  3. 3-Keto-L-gulofuranolactone
  4. 3-Oxo-L-gulofuranolactone
  5. Adenex
  6. Allercorb
  7. Antiscorbic vitamin
  8. Antiscorbutic vitamin
  9. Arco-cee
  10. Ascoltin
  11. Ascor-B.I.D.
  12. Ascorb
  13. Ascorbajen
  14. Ascorbate
  15. Ascorbic acid
  16. Ascorbicab
  17. Ascorbicap
  18. Ascorbicin
  19. Ascorbin
  20. Ascorbutina
  21. Ascorin
  22. Ascorteal
  23. Ascorvit
  24. C-level
  25. C-long
  26. C-quin
  27. C-span
  28. C-vimin
  29. Cantan
  30. Cantaxin
  31. Catavin C
  32. Ce lent
  33. Ce-mi-lin
  34. Ce-vi-sol
  35. Cebicure
  36. Cebid
  37. Cebion
  38. Cebione
  39. Cecon
  40. Cee-caps TD
  41. Cee-vite
  42. Cegiolan
  43. Ceglion
  44. Ceklin
  45. Celaskon
  46. Celin
  47. Cell C
  48. Cemagyl
  49. Cemill
  50. Cenetone
  51. Cenolate
  52. Cereon
  53. Cergona
  54. Cescorbat
  55. Cetamid
  56. Cetane
  57. Cetane-caps TC
  58. Cetane-caps TD
  59. Cetebe
  60. Cetemican
  61. Cevalin
  62. Cevatine
  63. Cevex
  64. Cevi-bid
  65. Cevimin
  66. Cevital
  67. Cevitamate
  68. Cevitamic acid
  69. Cevitamin
  70. Cevitan
  71. Cevitex
  72. Cewin
  73. Chewcee
  74. Ciamin
  75. Cipca
  76. Citriscorb
  77. Citrovit
  78. Colascor
  79. Concemin
  80. Davitamon C
  81. Dora-C-500
  82. Duoscorb
  83. Ferrous ascorbate
  84. HiCee
  85. Hybrin
  86. Ido-C
  87. Juvamine
  88. Kangbingfeng
  89. Kyselina askorbova
  90. L(+)-ascorbate
  91. L(+)-ascorbic acid
  92. L-(+)-ascorbate
  93. L-(+)-ascorbic acid
  94. L-3-Ketothreohexuronic acid lactone
  95. L-Ascorbic acid
  96. L-ascorbate
  97. L-lyxoascorbate
  98. L-lyxoascorbic acid
  99. L-threo-ascorbic acid
  100. L-xyloascorbate
  101. L-xyloascorbic acid
  102. Laroscorbine
  103. Lemascorb
  104. Liqui-cee
  105. Meri-c
  106. Natrascorb
  107. Natrascorb injectable
  108. Planavit C
  109. Proscorbin
  110. Redoxon
  111. Ribena
  112. Ronotec 100
  113. Rontex 100
  114. Roscorbic
  115. Rovimix C
  116. Scorbacid
  117. Scorbu C
  118. Scorbu-C
  119. Secorbate
  120. Sodascorbate
  121. Suncoat VC 40
  122. Testascorbic
  123. VASC
  124. Vicelat
  125. Vicin
  126. Vicomin C
  127. Viforcit
  128. Viscorin
  129. Viscorin 100M
  130. Vitace
  131. Vitacee
  132. Vitacimin
  133. Vitacin
  134. Vitamin C
  135. Vitamisin
  136. Vitascorbol
  137. Xitix
  138. gamma-lactone L-threo-Hex-2-enonate
  139. gamma-lactone L-threo-Hex-2-enonic acid
  140. (+)-Sodium L-ascorbate
Chemical IUPAC Name (2S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-furan-3-one
Chemical Formula C6H8O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Hydroxy Acids
Sub Class
  • Short chain hydroxy acids
Family
  • Food_Additive
Species
  • ketone; primary alcohol; secondary alcohol; 1,2-diol; heterocyclic compound
Biofunction
  • Essential vitamins; Anti-oxidant; Enzyme co-factor; Component of Tyrosine metabolism
Application
Source
  • Exogenous
Average Molecular Weight 176.124
Monoisotopic Molecular Weight 176.032089
Isomeric SMILES OC[C@@H](O)[C@@H]1OC(O)=C(O)C1=O
Canonical SMILES OCC(O)C1OC(O)=C(O)C1=O
KEGG Compound ID C00072 Link Image
BioCyc ID ASCORBATE Link Image
BiGG ID 33747 Link Image
Wikipedia Link Ascorbic acid Link Image
METLIN ID 3753 Link Image
PubChem Compound 644104 Link Image
PubChem Substance 15971359 Link Image
ChEBI ID 29073 Link Image
CAS Registry Number 50-81-7
InChI Identifier InChI=1/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8,10-11H,1H2/t2-,5+/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) 191 oC
Experimental Water Solubility 400 mg/mL at 40 oC [MERCK INDEX (1996)] Source: PhysProp
Predicted Water Solubility 257.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity -1.85 [AVDEEF,A (1997)] Source: PhysProp
Predicted LogP/Hydrophobicity -0.5 [Predicted by PubChem via XLOGP]; -1.87 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID 1E71 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Show Image
Show Peaklist
BMRB Spectrum Show Image
Show Peaklist
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location
  • Breast_Milk
Tissue Location
Tissue References
Adipose Tissue
Adrenal Cortex
Adrenal Medulla
Bladder
Brain
Epidermis
Erythrocyte
Eye Lens
Fibroblasts
Gonads
Heart
Intestine
Liver
Lung
Lymphocyte
Most Tissues
Muscle
Myelin
Neuron
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Concentrations (Normal)
Biofluid Breast_Milk
Value 153.301 uM
Age N/A
Sex N/A
Condition Normal
Comments Raw. Sampled during March.
References
Biofluid Breast_Milk
Value 22.711 +/- 1.419 uM
Age N/A
Sex N/A
Condition Normal
Comments Pasteurized.
References
Biofluid Breast_Milk
Value 33.499 +/- 1.703 uM
Age N/A
Sex N/A
Condition Normal
Comments Raw.
References
Biofluid Breast_Milk
Value 11.356 uM
Age N/A
Sex N/A
Condition Normal
Comments Milk, fluid, partly skimmed, 2% milkfat.
References
Biofluid Breast_Milk
Value 85.167 uM
Age N/A
Sex N/A
Condition Normal
Comments Milk, fluid, whole, producer, 3.7% milkfat.
References
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image