Record Information
Version1.0
Creation date2010-04-08 22:08:04 UTC
Update date2019-11-26 03:02:36 UTC
Primary IDFDB008424
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 is a very strong basic compound (based on its pKa). Thiamine exists in all living species, ranging from bacteria to humans. Thiamine is a bitter tasting compound. Thiamine is found, on average, in the highest concentration within a few different foods, such as spread, leavening agents, and meat bouillons and in a lower concentration in black walnuts, kales, and catjang pea. Thiamine has also been detected, but not quantified in, several different foods, such as meatballs, chewing gums, sakes, cooking oils, and babassu palms. This could make thiamine a potential biomarker for the consumption of these foods. Thiamine is a potentially toxic compound.
CAS Number70-16-6
Structure
Thumb
Synonyms
SynonymSource
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
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium(1+), 9CI, 8CIdb_source
Aneurinedb_source
Oryzanindb_source
Torulindb_source
Vitamin B1db_source
Vitaneurindb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H17N4OS
IUPAC name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
InChI IdentifierInChI=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
Isomeric SMILESCC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N
Average Molecular Weight265.355
Monoisotopic Molecular Weight265.112306876
Classification
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.32%; H 6.46%; N 21.11%; O 6.03%; S 12.08%DFC
Melting Point248 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 5.17DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-3890000000-9f8b525433ab279ad512JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9442000000-05ab93d3afb7b6f538e9JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0109000000-48864f31ba475645654bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05o1-9200000000-2ec0f3e9e364cffde16eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-0184506492d9f5b68b97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0090000000-872150be83cbd75d8ecfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0930000000-ecf71c75bdea859139d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-0900000000-4d9113fdc633fb1ccbb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-0900000000-4a8016299623af0c3027JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-1900000000-773912c9f325c419c77dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0390000000-95f3ca57c95542bdc7e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-e079d1fc1e06396dc524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0900000000-ebb16d4f204f291b9a3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00e9-4900000000-ad4d4779d76b9edb7ec5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9600000000-b631eed5be831527fc17JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-50f2f613f576814eb627JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-002b-0900000000-2f184bbfec6bc0ef00c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-9000000000-35bc744495a2570a565fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-1900000000-d8a7ac327273c32b4524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-0920000000-ca80ef6513c61be5b5e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0090000000-872150be83cbd75d8ecfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-183af2449d1439af9825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-2230ebc7c6b73192c26fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7920000000-75670df9647a475ca92cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3090000000-d0ff9a733629a86b75c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-3690000000-db3f204af490d7e1722eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9000000000-5196f2b4daab995967bfJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID1130
Pubchem Substance IDNot Available
ChEBI ID18385
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDKN09-S:DKN09-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDThiamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.