Thiamine triphosphate (BioDeep_00000005068)

 

Secondary id: BioDeep_00001869285

human metabolite Endogenous


代谢物信息卡片


3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium

化学式: C12H20N4O10P3S+ (505.0113)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 26.76%

分子结构信息

SMILES: CC1=C(CCOP(O)(=O)OP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1
InChI: InChI=1S/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23)/p+1

描述信息

Thiamine triphosphate is the triphosphate ester of thiamine. Thiamine triphosphate (ThTP) was previously considered to be a specific neuroactive form of thiamine. However, it was recently shown that ThTP exists in bacteria, fungi, plants and animals suggesting a much more general cellular role. In particular, it seems to play a role in response to amino acid starvation. In mammals, ThTP is hydrolyzed by a specific thiamine triphosphatase. In Leighs disease, this compound is present in decreased amounts in the brain due to a metabolic block in its formation. [HMDB]
Thiamine triphosphate is the triphosphate ester of thiamine. Thiamine triphosphate (ThTP) was previously considered to be a specific neuroactive form of thiamine. However, it was recently shown that ThTP exists in bacteria, fungi, plants and animals suggesting a much more general cellular role. In particular, it seems to play a role in response to amino acid starvation. In mammals, ThTP is hydrolyzed by a specific thiamine triphosphatase. In Leighs disease, this compound is present in decreased amounts in the brain due to a metabolic block in its formation.
D018977 - Micronutrients > D014815 - Vitamins

同义名列表

14 个代谢物同义名

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium; 3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-{2-[(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)oxy]ethyl}-4-methyl-1,3-thiazol-3-ium; 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,8,8-trihydroxy-4,6,8-trioxido-3,5,7-trioxa-4,6,8-triphosphaoct-1-yl)-thiazolium; Thiamine triphosphoric acid ester; Thiamine triphosphoric acid; Thiamine triphosphate ester; Thiamin triphosphoric acid; Triphosphate, thiamine; Triphosphate, thiamin; Thiamine triphosphate; Thiamin triphosphate; THTP; TTP; Thiamin triphosphate



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

32 个相关的代谢反应过程信息。

Reactome(28)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(4)

  • Thiamine Metabolism: Adenosine triphosphate + Thiamine ⟶ Adenosine monophosphate + Thiamine pyrophosphate
  • Thiamine Metabolism: Adenosine triphosphate + Thiamine ⟶ Adenosine monophosphate + Thiamine pyrophosphate
  • Thiamine Metabolism: Adenosine triphosphate + Thiamine ⟶ Adenosine monophosphate + Thiamine pyrophosphate
  • Thiamine Metabolism: Adenosine triphosphate + Thiamine ⟶ Adenosine monophosphate + Thiamine pyrophosphate

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 12 AK1, AXIN2, DPYSL5, HPGDS, PC, PRKX, PRNP, RAPSN, RELA, TBP, THTPA, ZMYND8
Endoplasmic reticulum membrane 2 PNMT, TKT
Mitochondrion membrane 1 PNMT
Nucleus 6 AXIN2, PLCZ1, PRKX, RELA, TBP, ZMYND8
cytosol 13 AK1, AXIN2, DPYSL5, HPGDS, PC, PLCZ1, PNMT, PRNP, RAPSN, RELA, THTPA, TKT, TPK1
dendrite 2 DPYSL5, PRNP
mitochondrial membrane 1 PNMT
nuclear body 1 TKT
centrosome 2 AXIN2, RAPSN
nucleoplasm 8 ATP2B1, HPGDS, PLCZ1, PRKX, RELA, TBP, TKT, ZMYND8
Cell membrane 3 ATP2B1, PRNP, TKT
Multi-pass membrane protein 2 ATP2B1, PNMT
Synapse 3 ATP2B1, RAPSN, SLITRK1
cell surface 1 PRNP
dendritic shaft 1 ZMYND8
glutamatergic synapse 4 ATP2B1, DPYSL5, RELA, SLITRK1
Golgi apparatus 2 PRNP, RAPSN
mitochondrial inner membrane 1 ATP5ME
neuromuscular junction 1 RAPSN
neuronal cell body 1 DPYSL5
postsynapse 1 PRNP
presynaptic membrane 1 ATP2B1
plasma membrane 6 ATP2B1, AXIN2, PRNP, RAPSN, SLITRK1, TKT
synaptic vesicle membrane 1 ATP2B1
terminal bouton 1 PRNP
Membrane 3 ATP2B1, PRNP, SLITRK1
apical plasma membrane 1 TKT
basolateral plasma membrane 1 ATP2B1
extracellular exosome 4 AK1, ATP2B1, PRNP, TKT
endoplasmic reticulum 2 PNMT, PRNP
perinuclear region of cytoplasm 1 PLCZ1
mitochondrion 5 ATP5ME, PC, PDK3, PNMT, PRNP
protein-containing complex 2 DPYSL5, TBP
intracellular membrane-bounded organelle 4 ATP2B1, HPGDS, PNMT, PRNP
postsynaptic density 1 PRNP
pronucleus 1 PLCZ1
Single-pass type I membrane protein 2 SLITRK1, TKT
Secreted 1 SLITRK1
extracellular region 1 SLITRK1
Mitochondrion outer membrane 1 PRNP
Single-pass membrane protein 1 PRNP
mitochondrial outer membrane 1 PRNP
Mitochondrion matrix 1 PC
mitochondrial matrix 2 PC, PDK3
transcription regulator complex 1 RELA
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
nuclear membrane 1 PRNP
external side of plasma membrane 1 PRNP
actin cytoskeleton 1 TKT
dendritic spine 1 ZMYND8
beta-catenin destruction complex 1 AXIN2
nucleolus 3 PDK3, PLCZ1, ZMYND8
vesicle 1 TKT
Cytoplasm, perinuclear region 1 PLCZ1
Membrane raft 1 PRNP
focal adhesion 1 TKT
GABA-ergic synapse 1 SLITRK1
Peroxisome 1 TKT
lateral plasma membrane 1 ATP2B1
receptor complex 1 TKT
chromatin 3 RELA, TBP, ZMYND8
cell projection 1 ATP2B1
Chromosome 1 ZMYND8
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 PRNP
female germ cell nucleus 1 TBP
[Isoform 1]: Endoplasmic reticulum membrane 1 PNMT
euchromatin 1 TBP
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 PRNP
male germ cell nucleus 1 TBP
transcription factor TFIID complex 1 TBP
extrinsic component of membrane 1 PRNP
postsynaptic density membrane 1 SLITRK1
immunological synapse 1 ATP2B1
postsynaptic specialization membrane 1 RAPSN
female pronucleus 1 TBP
male pronucleus 1 TBP
[Isoform 2]: Endoplasmic reticulum membrane 1 PNMT
site of DNA damage 1 ZMYND8
proton-transporting ATP synthase complex 1 ATP5ME
outer dense fiber 1 AK1
proton-transporting ATP synthase complex, coupling factor F(o) 1 ATP5ME
sperm head 1 PLCZ1
inclusion body 1 PRNP
photoreceptor ribbon synapse 1 ATP2B1
NF-kappaB p50/p65 complex 1 RELA
RNA polymerase transcription factor SL1 complex 1 TBP
transcription factor TFIIA complex 1 TBP
NF-kappaB complex 1 RELA


文献列表

  • Aymeric Goyer, Ghulam Hasnain, Océane Frelin, Maria A Ralat, Jesse F Gregory, Andrew D Hanson. A cross-kingdom Nudix enzyme that pre-empts damage in thiamin metabolism. The Biochemical journal. 2013 Sep; 454(3):533-42. doi: 10.1042/bj20130516. [PMID: 23834287]
  • Iu M Parkhomenko, A A Strokina, S Iu Pilipchuk, S P Stepanenko, L I Chekhovskaia, G V Donchenko. [Existence of two different active sites on thiamine binding protein in plasma membranes of synaptosomes]. Ukrains'kyi biokhimichnyi zhurnal (1999 ). 2010 Jan; 82(1):34-41. doi: . [PMID: 20684226]
  • Michel Frédérich, David Delvaux, Tiziana Gigliobianco, Marjorie Gangolf, Georges Dive, Gabriel Mazzucchelli, Benjamin Elias, Edwin De Pauw, Luc Angenot, Pierre Wins, Lucien Bettendorff. Thiaminylated adenine nucleotides. Chemical synthesis, structural characterization and natural occurrence. The FEBS journal. 2009 Jun; 276(12):3256-68. doi: 10.1111/j.1742-4658.2009.07040.x. [PMID: 19438713]
  • A A Sidorova, S P Stepanenko, Iu M Parkhomenko. [Characteristics of thiamine triphosphatase from neural cells plasma membranes]. Ukrains'kyi biokhimichnyi zhurnal (1999 ). 2009 May; 81(3):57-65. doi: NULL. [PMID: 19877430]
  • Iu M Parkhomenko, S Iu Pilipchuk, A A Sidorova, S P Stepanenko, L I Chekhovskaia, G V Donchenko. [Thiamine metabolism disorders in the rat brain in experimental alcoholism and a possibility of their correction by vitamin E]. Ukrains'kyi biokhimichnyi zhurnal (1999 ). 2008 Jul; 80(4):96-104. doi: . [PMID: 19140455]
  • Marie-Laure Volvert, Sandrine Seyen, Marie Piette, Brigitte Evrard, Marjorie Gangolf, Jean-Christophe Plumier, Lucien Bettendorff. Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives. BMC pharmacology. 2008 Jun; 8(?):10. doi: 10.1186/1471-2210-8-10. [PMID: 18549472]
  • S Bäckermann, C Poel, W Ternes. Thiamin phosphates in egg yolk granules and plasma of regular and embryonated eggs of hens and in five- and seven-day-old embryos. Poultry science. 2008 Jan; 87(1):108-15. doi: 10.3382/ps.2007-00158. [PMID: 18079459]
  • Hiroshi Ihara, Takayuki Matsumoto, Yoshio Shino, Naotaka Hashizume. Assay values for thiamine or thiamine phosphate esters in whole blood do not depend on the anticoagulant used. Journal of clinical laboratory analysis. 2005; 19(5):205-8. doi: 10.1002/jcla.20079. [PMID: 16170809]
  • O R Ianchiĭ, Iu M Parkhomenko, G V Donchenko. [Intracellular localization of thiamine-binding proteins in the liver and kidneys of rats]. Ukrains'kyi biokhimichnyi zhurnal (1999 ). 2003 Nov; 75(6):111-4. doi: NULL. [PMID: 15143527]
  • Alexander F Makarchikov, Pierre Wins, Edwin Janssen, Bé Wieringa, Thierry Grisar, Lucien Bettendorff. Adenylate kinase 1 knockout mice have normal thiamine triphosphate levels. Biochimica et biophysica acta. 2002 Oct; 1592(2):117-21. doi: 10.1016/s0167-4889(02)00277-x. [PMID: 12379473]
  • A F Makarchikov, I P Chernikevich. Thiamine triphosphatase activity in bovine kidney. Biochemistry and molecular biology international. 1998 Sep; 46(1):115-23. doi: 10.1080/15216549800203622. [PMID: 9784846]
  • Y Egi, S Koyama, T Shioda, K Yamada, T Kawasaki. Identification, purification and reconstitution of thiamin metabolizing enzymes in human red blood cells. Biochimica et biophysica acta. 1992 Nov; 1160(2):171-8. doi: 10.1016/0167-4838(92)90004-w. [PMID: 1332781]
  • C M Tallaksen, T Bøhmer, H Bell. Blood and serum thiamin and thiamin phosphate esters concentrations in patients with alcohol dependence syndrome before and after thiamin treatment. Alcoholism, clinical and experimental research. 1992 Apr; 16(2):320-5. doi: 10.1111/j.1530-0277.1992.tb01384.x. [PMID: 1317136]
  • B L Lee, H Y Ong, C N Ong. Determination of thiamine and its phosphate esters by gradient-elution high-performance liquid chromatography. Journal of chromatography. 1991 Jun; 567(1):71-80. doi: 10.1016/0378-4347(91)80311-y. [PMID: 1918262]
  • C M Tallaksen, T Bøhmer, H Bell, J Karlsen. Concomitant determination of thiamin and its phosphate esters in human blood and serum by high-performance liquid chromatography. Journal of chromatography. 1991 Mar; 564(1):127-36. doi: 10.1016/0378-4347(91)80075-n. [PMID: 1860908]
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  • L Bettendorff, L Weekers, P Wins, E Schoffeniels. Injection of sulbutiamine induces an increase in thiamine triphosphate in rat tissues. Biochemical pharmacology. 1990 Dec; 40(11):2557-60. doi: 10.1016/0006-2952(90)90099-7. [PMID: 2268373]
  • T Matsuda, H Tonomura, A Baba, H Iwata. Tissue difference in cellular localization of thiamine phosphate esters. Comparative biochemistry and physiology. B, Comparative biochemistry. 1989; 94(2):405-9. doi: 10.1016/0305-0491(89)90364-7. [PMID: 2591202]
  • L Bettendorff, C Grandfils, C De Rycker, E Schoffeniels. Determination of thiamine and its phosphate esters in human blood serum at femtomole levels. Journal of chromatography. 1986 Oct; 382(?):297-302. doi: 10.1016/s0378-4347(00)83533-1. [PMID: 3782398]
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  • C Patrini, G Rindi. An improved method for the electrophoretic separation and fluorometric determination of thiamine and its phosphates in animal tissues. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1980; 50(1):10-8. doi: NULL. [PMID: 7390709]
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