Thiamine
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Basic Info
| Common Name | Thiamine(F04732) |
| 2D Structure | |
| Description | Thiamine 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. Thiamine was first discovered by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. 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. |
| FRCD ID | F04732 |
| CAS Number | 59-43-8 |
| PubChem CID | 1130 |
| Formula | C12H17N4OS+ |
| IUPAC Name | 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol |
| 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 |
| Canonical SMILES | CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO |
| Isomeric SMILES | CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO |
| Wikipedia | Thiamine |
| Synonyms |
thiamine
thiaminium
thiamin
vitamin B1
Aneurin
Antiberiberi factor
Thiadoxine
Betaxin
Vitaneuron
Bequin
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Diazines |
| Subclass | Pyrimidines and pyrimidine derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Thiamines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as thiamines. These 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 265.355 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 269 |
| Monoisotopic Mass | 265.112 |
| Exact Mass | 265.112 |
| XLogP | 1 |
| Formal Charge | 1 |
| Heavy Atom Count | 18 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Rice flakes produced from commercial wild rice: Chemical compositions, vitamin B compounds, mineral and trace element contents and their dietary intake evaluation. | Food Chem | 2018 Oct 30 | 29853391 |
| In vitro evaluation of dietary compounds to reduce mercury bioavailability. | Food Chem | 2018 May 15 | 29329865 |
| Postnatal development of bitter taste avoidance behavior in mice is associated with ACTIN-dependent localization of bitter taste receptors to the microvilli of taste cells. | Biochem Biophys Res Commun | 2018 Jan 22 | 29278699 |
| Antioxidant, angiotensin-converting enzyme inhibitory activity and otherfunctional properties of egg white proteins and their derived peptides - Areview. | Poult Sci | 2018 Apr 1 | 29340654 |
| Beyond drug-drug interactions: effects of transporter inhibition on endobiotics, nutrients and toxins. | Expert Opin Drug Metab Toxicol | 2017 Oct | 28847160 |
| Reduced activities of thiamine-dependent and cytochrome c oxidase enzymes incerebral cortex of cattle affected by sulfur-induced polioencephalomalacia. | Can J Vet Res | 2017 Oct | 29081580 |
| The influence of infantile thiamine deficiency on primary dentition. | Clin Oral Investig | 2017 May | 27312377 |
| In vitro toxicity of pirimiphos-methyl in Atlantic salmon hepatocytes. | Toxicol In Vitro | 2017 Mar | 27845199 |
| A pilot study into a possible relationship between diet and stuttering. | J Fluency Disord | 2017 Jun | 28576291 |
| Physiochemical and cytotoxicity study of TPGS stabilized nanoemulsion designed by ultrasonication method. | Ultrason Sonochem | 2017 Jan | 27773233 |
| Comparative investigation of methionine and novel formulation Metovitanprotective effects in Wistar rats with testicular and epididymal toxicity inducedby anti-tuberculosis drugs co-administration. | Food Chem Toxicol | 2017 Jan | 27919644 |
| A combination of quantitative marinating and Maillard reaction to enhancevolatile flavor in Chinese marinated chicken. | J Sci Food Agric | 2017 Feb | 27185418 |
| High-concentrate diets based on forages harvested at different maturity stagesaffect ruminal synthesis of B vitamins in lactating dairy cows. | Animal | 2017 Apr | 27573890 |
| Nutrient patterns and their relationship to metabolic syndrome in Iranian adults. | Eur J Clin Invest | 2016 Oct | 27529331 |
| Factors associated with not meeting the recommendations for micronutrient intake in critically ill children. | Nutrition | 2016 Nov-Dec | 27262979 |
| Relationship between thiamine and subacute ruminal acidosis induced by ahigh-grain diet in dairy cows. | J Dairy Sci | 2016 Nov | 27568043 |
| Spontaneous poisoning by Hovenia dulcis in dairy cattle in Southwest Parana, Brazil. | Trop Anim Health Prod | 2016 Jan | 26415955 |
| Nutrition-adaptive control of multiple-bacteriocin production by Weissellahellenica QU 13. | J Appl Microbiol | 2016 Jan | 26538298 |
| Nutritional and Protein Deficiencies in the Short Term following Both GastricBypass and Gastric Banding. | PLoS One | 2016 Feb 18 | 26891123 |
| Complementary Feeding Diets Made of Local Foods Can Be Optimized, but Additional Interventions Will Be Needed to Meet Iron and Zinc Requirements in 6- to23-Month-Old Children in Low- and Middle-Income Countries. | Food Nutr Bull | 2016 Dec | 27334774 |
Targets
- General Function:
- Thiamine 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 Da
- Mechanism of Action:
- It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux.
References
- Pylypchuk SIu, Parkhomenko IuM, Protasova ZS, Vovk AI, Donchenko HV: [Interaction of rat brain thiamine kinase with thiamine and its derivatives]. Ukr Biokhim Zh. 2001 Mar-Apr;73(2):51-6. [11642045 ]
- General Function:
- Transketolase 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 Da
References
- Thomas AA, De Meese J, Le Huerou Y, Boyd SA, Romoff TT, Gonzales SS, Gunawardana I, Kaplan T, Sullivan F, Condroski K, Lyssikatos JP, Aicher TD, Ballard J, Bernat B, DeWolf W, Han M, Lemieux C, Smith D, Weiler S, Wright SK, Vigers G, Brandhuber B: Non-charged thiamine analogs as inhibitors of enzyme transketolase. Bioorg Med Chem Lett. 2008 Jan 15;18(2):509-12. doi: 10.1016/j.bmcl.2007.11.098. Epub 2007 Dec 3. [18182286 ]
- General Function:
- Thiamine uptake transmembrane transporter activity
- Specific Function:
- High-affinity transporter for the intake of thiamine.
- Gene Name:
- SLC19A2
- Uniprot ID:
- O60779
- Molecular Weight:
- 55399.49 Da
- Mechanism of Action:
- It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux.
- General Function:
- Thiamine uptake transmembrane transporter activity
- Specific Function:
- Mediates high affinity thiamine uptake, propably via a proton anti-port mechanism. Has no folate transport activity.
- Gene Name:
- SLC19A3
- Uniprot ID:
- Q9BZV2
- Molecular Weight:
- 55664.265 Da
- Mechanism of Action:
- It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux.