Record Information
Version2.0
Creation Date2012-05-31 10:24:24 -0600
Update Date2015-10-02 02:25:47 -0600
Secondary Accession Numbers
  • ECMDB00235
Identification
Name:Thiamine
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. It is a metabolite in E. coli, a substrate for enzyme thiamin kinase (gene name: thiK) which catalyzes the chemical reaction thiamin + ATP -> thiamin phosphate + ADP + H+ (EcoCyc compound: THIAMINE).
Structure
Thumb
Synonyms:
  • Aneurin
  • Antiberiberi factor
  • Apate drops
  • Apic acid drops
  • Beatine
  • Bedome
  • Begiolan
  • Benerva
  • Bequin
  • Berin
  • Betalin S
  • Betaxin
  • Bethiazine
  • Beuion
  • Bevitex
  • Bevitine
  • Bewon
  • Biamine
  • Bithiamin
  • Biuno
  • Bivatin
  • Bivita
  • Cernevit-12
  • Clotiamina
  • Eskapen
  • Eskaphen
  • Hybee
  • Lixa-b
  • Lixa-beta
  • Lixa-β
  • Metabolin
  • Slowten
  • THD
  • Thiadoxine
  • Thiamin
  • Thiaminal
  • Thiamine
  • Thiaminium
  • Thiamol
  • Thiavit
  • Tiamidon
  • Tiaminal
  • Trophite
  • Vetalin S
  • VIB
  • Vinothiam
  • Vitamin B1
  • Vitamin B1
  • Vitaneuron
Chemical Formula:C12H17N4OS
Weight:Average: 265.355
Monoisotopic: 265.112306876
InChI Key:JZRWCGZRTZMZEH-UHFFFAOYSA-N
InChI: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
CAS number:59-43-8
IUPAC Name:3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Name:thiamine
SMILES:CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamines
Alternative Parents
Substituents
  • Thiamine
  • 4,5-disubstituted 1,3-thiazole
  • Aminopyrimidine
  • Imidolactam
  • Azole
  • Thiazole
  • Heteroaromatic compound
  • Azacycle
  • Alcohol
  • Organopnictogen compound
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:248 °C
Experimental Properties:
PropertyValueSource
Water Solubility:500.0 mg/mL [MERCK INDEX (1996)]PhysProp
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 Area75.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.4 m³·mol⁻¹ChemAxon
Polarizability28.14 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-3890000000-9f8b525433ab279ad512View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9442000000-05ab93d3afb7b6f538e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0109000000-48864f31ba475645654bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05o1-9200000000-2ec0f3e9e364cffde16eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-0184506492d9f5b68b97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0090000000-872150be83cbd75d8ecfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0930000000-ecf71c75bdea859139d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-0900000000-4d9113fdc633fb1ccbb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-0900000000-4a8016299623af0c3027View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-1900000000-773912c9f325c419c77dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0390000000-95f3ca57c95542bdc7e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-e079d1fc1e06396dc524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0900000000-ebb16d4f204f291b9a3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00e9-4900000000-ad4d4779d76b9edb7ec5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9600000000-b631eed5be831527fc17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-50f2f613f576814eb627View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-002b-0900000000-2f184bbfec6bc0ef00c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-9000000000-35bc744495a2570a565fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-1900000000-d8a7ac327273c32b4524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-0920000000-ca80ef6513c61be5b5e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0090000000-872150be83cbd75d8ecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-183af2449d1439af9825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-2230ebc7c6b73192c26fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7920000000-75670df9647a475ca92cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3090000000-d0ff9a733629a86b75c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-3690000000-db3f204af490d7e1722eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9000000000-5196f2b4daab995967bfView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • Pedraza OL, Botez MI: Thiamine status in inherited degenerative ataxias. J Neurol Neurosurg Psychiatry. 1992 Feb;55(2):136-7. Pubmed: 1538220
  • 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
  • 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
  • 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
  • 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
  • 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
  • Singleton CK, Martin PR: Molecular mechanisms of thiamine utilization. Curr Mol Med. 2001 May;1(2):197-207. Pubmed: 11899071
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18385
HMDB IDHMDB00235
Pubchem Compound ID1130
Kegg IDC00378
ChemSpider ID1098
WikipediaThiamine
BioCyc IDTHIAMINE
EcoCyc IDTHIAMINE
Ligand ExpoVIB

Enzymes

General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Catalyzes the phosphorylation of thiamine to thiamine phosphate
Gene Name:
thiK
Uniprot ID:
P75948
Molecular weight:
32397
Reactions
ATP + thiamine = ADP + thiamine phosphate.
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex thiBPQ involved in thiamine import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
thiP
Uniprot ID:
P31549
Molecular weight:
59532
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex ThiBPQ involved in thiamine import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
thiQ
Uniprot ID:
P31548
Molecular weight:
24999
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex thiBPQ involved in thiamine import
Gene Name:
thiB
Uniprot ID:
P31550
Molecular weight:
36163

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex thiBPQ involved in thiamine import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
thiP
Uniprot ID:
P31549
Molecular weight:
59532
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex ThiBPQ involved in thiamine import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
thiQ
Uniprot ID:
P31548
Molecular weight:
24999
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex thiBPQ involved in thiamine import
Gene Name:
thiB
Uniprot ID:
P31550
Molecular weight:
36163