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Record Information
Version1.0
Creation Date2016-09-30 22:27:10 UTC
Update Date2020-06-04 20:45:42 UTC
MCDB ID BMDB0000235
Secondary Accession Numbers
  • BMDB00235
Metabolite Identification
Common NameThiamine
DescriptionThiamine, also known as vitamin B1 or aneurin, 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 is a drug which is used for the treatment of thiamine and niacin deficiency states, korsakov's alcoholic psychosis, wernicke-korsakov syndrome, delirium, and peripheral neuritis. Thiamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Thiamine exists in all living species, ranging from bacteria to humans. In cattle, thiamine is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway. Thiamine is a potentially toxic compound.
Structure
Thumb
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 Number59-43-8
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-3890000000-9f8b525433ab279ad5122016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9442000000-05ab93d3afb7b6f538e92017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0109000000-48864f31ba475645654b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05o1-9200000000-2ec0f3e9e364cffde16e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-0184506492d9f5b68b972012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0090000000-872150be83cbd75d8ecf2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0930000000-ecf71c75bdea859139d52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-0900000000-4d9113fdc633fb1ccbb52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-0900000000-4a8016299623af0c30272012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-1900000000-773912c9f325c419c77d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0390000000-95f3ca57c95542bdc7e72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-e079d1fc1e06396dc5242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0900000000-ebb16d4f204f291b9a3a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00e9-4900000000-ad4d4779d76b9edb7ec52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9600000000-b631eed5be831527fc172012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-50f2f613f576814eb6272012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-002b-0900000000-2f184bbfec6bc0ef00c62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-9000000000-35bc744495a2570a565f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-1900000000-d8a7ac327273c32b45242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-0920000000-ca80ef6513c61be5b5e92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0090000000-872150be83cbd75d8ecf2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-183af2449d1439af98252016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-2230ebc7c6b73192c26f2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7920000000-75670df9647a475ca92c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3090000000-d0ff9a733629a86b75c72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-3690000000-db3f204af490d7e1722e2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9000000000-5196f2b4daab995967bf2016-09-12View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1.131 uM details
Detected and Quantified1.131 uM details
Detected and Quantified0.754 uM details
Detected and Quantified1.357 uM details
Detected and Quantified0.754 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1.507 uM details
Detected and Quantified0.754 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1.545 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1.432 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1.507 uM details
Detected and Quantified1.696 uM details
Detected and Quantified1.47 uM details
Detected and Quantified1.47 uM details
Detected and Quantified1.734 uM details
Detected and Quantified1.734 uM details
Detected and Quantified1.696 uM
  • Park, Y. W; Juáre...
details
Detected and Quantified9 - 52 uM details
Detected and Quantified1.36 - 1.47 uM details
Detected and Quantified1.6 +/- 0.1 uM details
Detected and Quantified1.6 +/- 0.1 uM details
Detected and Quantified1.8 +/- 0.1 uM details
Detected and Quantified1.53 +/- 0.04 uM details
HMDB IDHMDB0000235
DrugBank IDDB00152
Phenol Explorer Compound IDNot Available
FoodDB 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
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. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
  2. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
  3. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  4. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  5. USDA Food Composition Databases [Link]