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Bovine Rumen Metabolome Database



Showing metabocard for Thiamine (RMDB00235)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-10-28 13:51:00
Accession Number RMDB00235
Common Name Thiamine
Description Thiamine or thiamin, also known as vitamin B1, is a colorless compound with the chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. thiamine plays an important role in helping the body convert carbohydrates and fat into energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue.
Synonyms
  1. Aneurin
  2. Antiberiberi factor
  3. Apate drops
  4. Beatine
  5. Bedome
  6. Begiolan
  7. Benerva
  8. Bequin
  9. Berin
  10. Betalin s
  11. Betaxin
  12. Bethiazine
  13. Beuion
  14. Bevitex
  15. Bevitine
  16. Bewon
  17. Biamine
  18. Bithiamin
  19. Biuno
  20. Bivatin
  21. Bivita
  22. Cernevit-12
  23. Clotiamina
  24. Eskapen
  25. Eskaphen
  26. Hybee
  27. Lixa-beta
  28. Metabolin
  29. Slowten
  30. THD
  31. Thiadoxine
  32. Thiamin
  33. Thiaminal
  34. Thiaminium
  35. Thiamol
  36. Thiavit
  37. Tiamidon
  38. Tiaminal
  39. Trophite
  40. Vetalin S
  41. VIB
  42. Vinothiam
  43. Vitamin B1
  44. Vitaneuron
Chemical IUPAC Name 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1-thia-3-azoniacyclopenta-2,4-dien-5-yl]ethanol
Chemical Formula C12H17N4OS
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellanous
Class
  • Thiazoles
Sub Class
  • Miscellaneous heterocyclic compounds
Family
  • Mammalian_Metabolite
Species
  • cation; primary alcohol; primary amine; primary aromatic amine; aromatic compound; heterocyclic compound
Biofunction
  • Essential vitamins; Component of Thiamine metabolism
Application
Source
  • Exogenous
Average Molecular Weight 265.355
Monoisotopic Molecular Weight 265.112305
Isomeric SMILES CC1=NC(N)=C(C[N+]2=CSC(CCO)=C2C)C=N1
Canonical SMILES CC1=NC(N)=C(C[N+]2=CSC(CCO)=C2C)C=N1
KEGG Compound ID C00378 Link Image
BioCyc ID THIAMINE Link Image
BiGG ID 34804 Link Image
Wikipedia Link Thiamine Link Image
METLIN ID 5242 Link Image
PubChem Compound 1130 Link Image
PubChem Substance 5645942 Link Image
ChEBI ID 18385 Link Image
CAS Registry Number 59-43-8
InChI Identifier InChI=1/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1
Synthesis Reference Sugimoto, Hirohiko; Ishiba, Teruyuki; Sato, Tomohiro; Nakai, Hiroshi; Hirai, Kentaro. Novel S-alkylation products from "isolated thiamin ylide" via thiaminium neothiaminthiolate ion pair. Journal of Organic Chemistry (1990), 55(2), 467-70.
Melting Point (Experimental) 248 oC
Experimental Water Solubility 500.0 mg/mL [MERCK INDEX (1996)] Source: PhysProp
Predicted Water Solubility 0.0153 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.11 [Predicted by ALOGPS]; 2.169 [Predicted by PubChem via XLOGP]; -3.93 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • Membrane (Predicted from LogP)
  • Extracellular
  • mitochondria
Biofluid Location
  • Rumen
  • Cow_Milk
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 1.6 uM
Age N/A
Sex Both
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
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