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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-13 01:06:24 UTC
HMDB IDHMDB00235
Secondary Accession NumbersNone
Metabolite Identification
Common NameThiamine
DescriptionThiamine 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.
Structure
Thumb
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 FormulaC12H17N4OS
Average Molecular Weight265.355
Monoisotopic Molecular Weight265.112306876
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Namethiamine
CAS Registry Number59-43-8
SMILES
CC1=C(CCO)SC=[N+]1CC1=C(N)N=C(C)N=C1
InChI Identifier
InChI=1S/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
InChI KeyJZRWCGZRTZMZEH-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassThiamines
Sub ClassN/A
Other Descriptors
  • Water-soluble vitamins(KEGG)
  • a vitamin(Cyc)
  • thiamine(ChEBI)
Substituents
  • Aminopyrimidine
  • Primary Alcohol
  • Pyrimidine
  • Thiazole
Direct ParentThiamines
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Thiamine metabolism
  • Essential vitamins
ApplicationNot Available
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.015 g/LALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-4.3ALOGPS
pKa (strongest acidic)15.5ChemAxon
pKa (strongest basic)5.54ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area75.91ChemAxon
rotatable bond count4ChemAxon
refractivity73.4ChemAxon
polarizability28.12ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Gland
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Placenta
  • Skeletal Muscle
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Thiamine MetabolismSMP00076map00730
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.34 (0.14-0.79) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.16 (0.06-0.41) uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.096 +/- 0.018 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.12 (0.094-0.280) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.006 (0.005 - 0.007) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.141 +/- 0.0543 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0487 +/- 0.00275 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.12 +/- 0.09 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.02 +/- 0.01 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.22 (0.20-0.60) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.035 +/- 0.006 uMElderly (>65 years old)Both
Hemodialysis
details
BloodDetected and Quantified0.18 +/- 0.066 uMAdult (>18 years old)BothFriedreich's ataxia details
BloodDetected and Quantified0.17 +/- 0.051 uMAdult (>18 years old)BothOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.115 +/- 0.0464 uMAdult (>18 years old)BothFriedreich's ataxia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0902 +/- 0.0411 uMAdult (>18 years old)BothOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.02 +/- 0.00 uMAdult (>18 years old)Not Specified
Alcoholism
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.00 uMAdult (>18 years old)Not Specified
Alcoholism
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.09 +/- 0.01 uMAdult (>18 years old)Not SpecifiedOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.06 +/- 0.01 uMAdult (>18 years old)Not SpecifiedAutosomal recessive spastic ataxia of Charlevoix-Saguena details
Cerebrospinal Fluid (CSF)Detected and Quantified0.1 +/- 0.01 uMNot SpecifiedNot SpecifiedFriedreich's ataxia details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. Pubmed: 182198
Friedreich's ataxia
  1. Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. Pubmed: 1538220
  2. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
Hemodialysis
  1. Hung SC, Hung SH, Tarng DC, Yang WC, Chen TW, Huang TP: Thiamine deficiency and unexplained encephalopathy in hemodialysis and peritoneal dialysis patients. Am J Kidney Dis. 2001 Nov;38(5):941-7. Pubmed: 11684545
Olivopontocerebral atrophy
  1. Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. Pubmed: 1538220
  2. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
Hereditary spastic paraplegia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. Pubmed: 11383938
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008425
KNApSAcK IDNot Available
Chemspider ID1098
KEGG Compound IDC00378
BioCyc IDTHIAMINE
BiGG ID34804
Wikipedia LinkThiamine
NuGOwiki LinkHMDB00235
Metagene LinkHMDB00235
METLIN ID5242
PubChem Compound1130
PDB IDVIB
ChEBI ID18385
References
Synthesis ReferenceSugimoto, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dutta B, Huang W, Molero M, Kekuda R, Leibach FH, Devoe LD, Ganapathy V, Prasad PD: Cloning of the human thiamine transporter, a member of the folate transporter family. J Biol Chem. 1999 Nov 5;274(45):31925-9. Pubmed: 10542220
  2. Bellazzi R, Guglielmann R, Ironi L, Patrini C: A hybrid input-output approach to model metabolic systems: an application to intracellular thiamine kinetics. J Biomed Inform. 2001 Aug;34(4):221-48. Pubmed: 11977806
  3. Pietrzak I, Baczyk K: Comparison of the thiamine level in blood and erythrocyte transketolase activity in hemodialyzed and nondialyzed patients during recombinant human erythropoietin therapy. Miner Electrolyte Metab. 1997;23(3-6):277-82. Pubmed: 9387133
  4. Singleton CK, Martin PR: Molecular mechanisms of thiamine utilization. Curr Mol Med. 2001 May;1(2):197-207. Pubmed: 11899071
  5. Sato Y, Nakagawa M, Higuchi I, Osame M, Naito E, Oizumi K: Mitochondrial myopathy and familial thiamine deficiency. Muscle Nerve. 2000 Jul;23(7):1069-75. Pubmed: 10883001
  6. Mastrogiacoma F, Bettendorff L, Grisar T, Kish SJ: Brain thiamine, its phosphate esters, and its metabolizing enzymes in Alzheimer's disease. Ann Neurol. 1996 May;39(5):585-91. Pubmed: 8619543
  7. Molina JA, Jimenez-Jimenez FJ, Hernanz A, Fernandez-Vivancos E, Medina S, de Bustos F, Gomez-Escalonilla C, Sayed Y: Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease. J Neural Transm. 2002 Jul;109(7-8):1035-44. Pubmed: 12111441
  8. Pietrzak I, Baczyk K, Kubiak W: Recombinant human erythropoietin administration improves thiamine content in blood and erythrocytes transketolase activity in pre-dialyzed patients. Ann Univ Mariae Curie Sklodowska [Med]. 1994;48 Suppl 3:29-37. Pubmed: 8192530
  9. Valerio G, Franzese A, Poggi V, Patrini C, Laforenza U, Tenore A: Lipophilic thiamine treatment in long-standing insulin-dependent diabetes mellitus. Acta Diabetol. 1999 Jun;36(1-2):73-6. Pubmed: 10436256
  10. Herve C, Beyne P, Delacoux E: Determination of thiamine and its phosphate esters in human erythrocytes by high-performance liquid chromatography with isocratic elution. J Chromatogr B Biomed Appl. 1994 Mar 4;653(2):217-20. Pubmed: 8205249
  11. Losa R, Sierra MI, Fernandez A, Blanco D, Buesa JM: Determination of thiamine and its phosphorylated forms in human plasma, erythrocytes and urine by HPLC and fluorescence detection: a preliminary study on cancer patients. J Pharm Biomed Anal. 2005 Apr 29;37(5):1025-9. Pubmed: 15862682
  12. Pietrzak I, Baczyk K, Mlynarczyk M: [The influence of intermittent peritoneal dialysis on free and total thiamine concentration in plasma and erythrocytes of patients with end stage renal disease] Pol Arch Med Wewn. 1994;92 Spec No:31-6. Pubmed: 7731897
  13. Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. Pubmed: 1538220
  14. Vinogradov VV, Tarasov IuA, Tishin VS, Bogdanovich VI, Spas VV: [Thiamine prevention of the corticosteroid reaction afer surgery] Probl Endokrinol (Mosk). 1981 May-Jun;27(3):11-6. Pubmed: 7291135
  15. Tanaka T, Sohmiya K, Kono T, Terasaki F, Horie R, Ohkaru Y, Muramatsu M, Takai S, Miyazaki M, Kitaura Y: Thiamine attenuates the hypertension and metabolic abnormalities in CD36-defective SHR: Uncoupling of glucose oxidation from cellular entry accompanied with enhanced protein O-GlcNAcylation in CD36 deficiency. Mol Cell Biochem. 2006 Apr 28;. Pubmed: 16645728
  16. Bettendorff L, Mastrogiacomo F, Kish SJ, Grisar T: Thiamine, thiamine phosphates, and their metabolizing enzymes in human brain. J Neurochem. 1996 Jan;66(1):250-8. Pubmed: 8522961
  17. Lee DC, Chu J, Satz W, Silbergleit R: Low plasma thiamine levels in elder patients admitted through the emergency department. Acad Emerg Med. 2000 Oct;7(10):1156-9. Pubmed: 11015250
  18. Shimon I, Almog S, Vered Z, Seligmann H, Shefi M, Peleg E, Rosenthal T, Motro M, Halkin H, Ezra D: Improved left ventricular function after thiamine supplementation in patients with congestive heart failure receiving long-term furosemide therapy. Am J Med. 1995 May;98(5):485-90. Pubmed: 7733128

Enzymes

General function:
Involved in thiamin diphosphokinase activity
Specific function:
Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate.
Gene Name:
TPK1
Uniprot ID:
Q9H3S4
Molecular weight:
27265.05
Reactions
Adenosine triphosphate + Thiamine → Adenosine monophosphate + Thiamine pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
General function:
Involved in adenylate cyclase activity
Specific function:
Hydrolase highly specific for thiamine triphosphate (ThTP).
Gene Name:
THTPA
Uniprot ID:
Q9BU02
Molecular weight:
25565.685
General function:
Involved in folic acid binding
Specific function:
High-affinity transporter for the intake of thiamine.
Gene Name:
SLC19A2
Uniprot ID:
O60779
Molecular weight:
55399.49
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A2
Uniprot ID:
Q7Z7J1
Molecular weight:
7567.7
General function:
Not Available
Specific function:
Not Available
Gene Name:
SLC19A2
Uniprot ID:
B0FBR7
Molecular weight:
1539.7
General function:
Involved in folic acid binding
Specific function:
Not Available
Gene Name:
SLC19A2
Uniprot ID:
Q5TIE1
Molecular weight:
51277.0
General function:
Involved in phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available