Showing metabocard for Thiamine (BMDB0000235)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:10 UTC
Update Date2020-06-04 20:45:42 UTC
BMDB IDBMDB0000235
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
MOLSDFPDBSMILESInChI
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
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
  • Mitochondria
  • Myelin sheath
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
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
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
  • Mitochondria
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Gland
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Neuron
  • Placenta
  • Ruminal Fluid
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot SpecifiedNormal
    • Park, Y. W; Juáre...
 details
MilkDetected and Quantified1.131 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.131 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.754 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.357 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.754 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.507 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.754 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.545 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.432 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.507 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.696 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.47 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.47 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.734 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.734 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.668 - 51.629 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified1.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.53 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.357 - 1.470 uMNot SpecifiedNot SpecifiedNormal details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified1.6 uMNot SpecifiedBothNormal details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000235
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
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)Not Available
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]

Enzymes

Enzyme Details
1. Thiamin pyrophosphokinase 1
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate (By similarity).
Gene Name:
TPK1
Uniprot ID:
Q5E9T4
Molecular weight:
27028.0
Reactions
Adenosine triphosphate + Thiamine → Adenosine monophosphate + Thiamine pyrophosphatedetails
Enzyme Details
2. Mitochondrial thiamine pyrophosphate carrier
General function:
Involved in binding
Specific function:
Mitochondrial transporter mediating uptake of thiamine pyrophosphate (ThPP) into mitochondria.
Gene Name:
SLC25A19
Uniprot ID:
Q29RM1
Molecular weight:
35112.0