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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000235
Secondary Accession Numbers
  • HMDB00235
Metabolite Identification
Common NameThiamine
DescriptionThiamine, also known as aneurin or vitamin B1, 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. Thiamine exists in all living species, ranging from bacteria to plants to humans. Thiamine biosynthesis occurs in bacteria, some protozoans, plants, and fungi. Thiamine is a vitamin and an essential nutrient meaning the body cannot synthesize it, and it must be obtained from the diet. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered in 1897 by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine was the first B vitamin to be isolated in 1926 and was first made in 1936. 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. Thiamine has antioxidant, erythropoietic, cognition-and mood-modulatory, antiatherosclerotic, putative ergogenic, and detoxification activities. Natural derivatives of thiamine, such as thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and adenosine thiamine triphosphate (AThTP), act as coenzymes in addition to performing unique biological functions. Thiamine deficiency can lead to beriberi, Wernicke-Korsakoff syndrome, optic neuropathy, Leigh's disease, African seasonal ataxia (or Nigerian seasonal ataxia), and central pontine myelinolysis. In Western countries, thiamine deficiency is seen mainly in chronic alcoholism. Thiamine supplements or thiamine therapy can be used for the treatment of a number of disorders including thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis. In humans, thiamine is involved in the metabolic disorder called 2-methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency. Outside of the human body, Thiamine is found in high quantities in whole grains, legumes, pork, fruits, and yeast and fish. Grain processing removes much of the thiamine content in grains, so in many countries cereals and flours are enriched with thiamine.
Structure
Data?1599761115
Synonyms
ValueSource
3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-iumChEBI
AneurinChEBI
Antiberiberi factorChEBI
ThiaminChEBI
Thiamine(1+) ionChEBI
ThiaminiumChEBI
Vitamin b1ChEBI
Apate dropsHMDB
BeatineHMDB
BedomeHMDB
BegiolanHMDB
BenervaHMDB
BequinHMDB
BerinHMDB
Betalin SHMDB
BetaxinHMDB
BethiazineHMDB
BeuionHMDB
BevitexHMDB
BevitineHMDB
BewonHMDB
BiamineHMDB
BithiaminHMDB
BiunoHMDB
BivatinHMDB
BivitaHMDB
Cernevit-12HMDB
ClotiaminaHMDB
EskapenHMDB
EskaphenHMDB
HybeeHMDB
Lixa-betaHMDB
MetabolinHMDB
SlowtenHMDB
THDHMDB
ThiadoxineHMDB
ThiaminalHMDB
ThiamolHMDB
ThiavitHMDB
TiamidonHMDB
TiaminalHMDB
TrophiteHMDB
Vetalin SHMDB
VIBHMDB
VinothiamHMDB
VitaneuronHMDB
Mononitrate, thiamineMeSH, HMDB
Thiamine mononitrateMeSH, HMDB
Vitamin b 1MeSH, HMDB
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 Namethiamine
CAS Registry Number70-16-6
SMILES
CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N
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
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg160.330932474
[M+H]+MetCCS_test_pos162.37330932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+158.59732859911
AllCCS[M-H]-163.75532859911
DeepCCS[M+H]+161.24130932474
DeepCCS[M-H]-158.88330932474
DeepCCS[M-2H]-192.23430932474
DeepCCS[M+Na]+167.35230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ThiamineCC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N3535.8Standard polar33892256
ThiamineCC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N2426.3Standard non polar33892256
ThiamineCC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N2498.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thiamine,1TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N)=N12471.7Semi standard non polar33892256
Thiamine,1TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N[Si](C)(C)C)=N12549.4Semi standard non polar33892256
Thiamine,2TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N12502.4Semi standard non polar33892256
Thiamine,2TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N12467.2Standard non polar33892256
Thiamine,2TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N13264.5Standard polar33892256
Thiamine,2TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N12540.1Semi standard non polar33892256
Thiamine,2TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N12549.2Standard non polar33892256
Thiamine,2TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N13162.5Standard polar33892256
Thiamine,3TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N12514.5Semi standard non polar33892256
Thiamine,3TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N12583.7Standard non polar33892256
Thiamine,3TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N12946.7Standard polar33892256
Thiamine,1TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N)=N12740.7Semi standard non polar33892256
Thiamine,1TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N[Si](C)(C)C(C)(C)C)=N12747.4Semi standard non polar33892256
Thiamine,2TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N12905.4Semi standard non polar33892256
Thiamine,2TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N12897.6Standard non polar33892256
Thiamine,2TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N13365.0Standard polar33892256
Thiamine,2TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N12927.6Semi standard non polar33892256
Thiamine,2TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N12959.6Standard non polar33892256
Thiamine,2TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCO)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N13242.0Standard polar33892256
Thiamine,3TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N13094.1Semi standard non polar33892256
Thiamine,3TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N13195.6Standard non polar33892256
Thiamine,3TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCO[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N13187.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-3890000000-9f8b525433ab279ad5122016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9442000000-05ab93d3afb7b6f538e92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-000i-0109000000-48864f31ba475645654b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-05o1-9200000000-2ec0f3e9e364cffde16e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0aou-9000000000-0184506492d9f5b68b972012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-03di-0090000000-872150be83cbd75d8ecf2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0002-0930000000-ecf71c75bdea859139d52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0002-0900000000-4d9113fdc633fb1ccbb52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0002-0900000000-4a8016299623af0c30272012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0002-1900000000-773912c9f325c419c77d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-014i-0390000000-95f3ca57c95542bdc7e72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00di-0900000000-e079d1fc1e06396dc5242012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00di-0900000000-ebb16d4f204f291b9a3a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00e9-4900000000-ad4d4779d76b9edb7ec52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-001i-9600000000-b631eed5be831527fc172012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0900000000-50f2f613f576814eb6272012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-002b-0900000000-2f184bbfec6bc0ef00c62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-001i-9000000000-35bc744495a2570a565f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-00di-1900000000-d8a7ac327273c32b45242012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0002-0920000000-ca80ef6513c61be5b5e92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine LC-ESI-QQ , negative-QTOFsplash10-03di-0090000000-872150be83cbd75d8ecf2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine 10V, Positive-QTOFsplash10-014i-0190000000-183af2449d1439af98252016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine 20V, Positive-QTOFsplash10-0a4i-0090000000-2230ebc7c6b73192c26f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine 40V, Positive-QTOFsplash10-0002-7920000000-75670df9647a475ca92c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine 10V, Negative-QTOFsplash10-03di-3090000000-d0ff9a733629a86b75c72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine 20V, Negative-QTOFsplash10-03dj-3690000000-db3f204af490d7e1722e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine 40V, Negative-QTOFsplash10-0005-9000000000-5196f2b4daab995967bf2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Placenta
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.12 (0.094-0.280) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.050-0.120 uMAdult (>18 years old)Both
Normal
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.247 +/- 0.006 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
UrineDetected and Quantified0.132 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0283 +/- 0.0191 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0511 +/- 0.0255 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
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 ]
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 ]
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 ]
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 ]
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 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB00152
Phenol Explorer Compound IDNot Available
FooDB IDFDB008424
KNApSAcK IDC00000775
Chemspider ID1098
KEGG Compound IDC00378
BioCyc IDTHIAMINE
BiGG IDNot Available
Wikipedia LinkThiamine
METLIN IDNot Available
PubChem Compound1130
PDB IDNot Available
ChEBI ID18385
Food Biomarker OntologyNot Available
VMH IDTHM
MarkerDB IDMDB00000114
Good Scents IDNot Available
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 (Vienna). 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. 2007 May;299(1-2):23-35. [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 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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