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Revision as of 20:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 399377256 of page Adenosine_thiamine_triphosphate for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 21:58, 30 June 2024 edit Teaktl17 (talk | contribs)Extended confirmed users17,864 editsm →top: bold for redirect target 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 399375402 | verifiedrevid = 477242483
| ImageFile = Adenosine thiamine triphosphate.png | ImageFile = Adenosine thiamine triphosphate.png
| ImageSize = 250px | ImageSize = 250px
| SystematicName = (2<sup>2</sup>''R'',2<sup>3</sup>''R'',2<sup>4</sup>''S'',2<sup>5</sup>''R'')-1<sup>6</sup>,13<sup>4</sup>-Diamino-2<sup>3</sup>,2<sup>4</sup>,5,7,9-pentahydroxy-13<sup>4</sup>,15<sup>2</sup>-dimethyl-5,7,9-trioxo-4,6,8,10-tetraoxa-5λ<sup>5</sup>,7λ<sup>5</sup>,9λ<sup>5</sup>-triphospha-13<sup>3</sup>λ<sup>5</sup>-1(9)-purina-15(5)-pyrimidina-13(5,3)-thiazola-2(2,5)-oxolanapentadecaphan-13<sup>3</sup>-ylium
| IUPACName = 3-((4-amino-2-methylpyrimidin-5-yl)methyl)-5-(2-(((((((((2''R'',3''S'',4''R'',5''R'')-5-(6-amino-9''H''-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethyl)-4-methylthiazol-3-ium
⚫ | OtherNames = ''P''<sup>1</sup>,''P''<sup>3</sup>-(Adenosine-5′-thiamine) triphosphate
| IUPACName_hidden = yes
⚫ | OtherNames = P1,P3-(Adenosine-5'-thiamine) triphosphate
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13082023 | ChemSpiderID = 13082023
| InChI = 1/C22H30N9O13P3S/c1-11-15(48-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-40-45(34,35)43-47(38,39)44-46(36,37)41-7-14-17(32)18(33)22(42-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H6-,23,24,25,26,27,29,34,35,36,37,38,39)/p+1/t14-,17-,18-,22-/m1/s1 | InChI = 1/C22H30N9O13P3S/c1-11-15(48-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-40-45(34,35)43-47(38,39)44-46(36,37)41-7-14-17(32)18(33)22(42-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H6-,23,24,25,26,27,29,34,35,36,37,38,39)/p+1/t14-,17-,18-,22-/m1/s1
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FGOYXNBJKMNPDH-SAJUPQAESA-O | StdInChIKey = FGOYXNBJKMNPDH-SAJUPQAESA-O
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 30632-11-2 --> | CASNo = 30632-11-2
⚫ | CASNo_Comment = (chloride)

⚫ | PubChem = 15938962
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES = NC1=NC=NC2=C1N=CN23(O)(O)(COP(OP(OP(OCCC4=C(C)(CC5=CN=C(C)N=C5N)=CS4)(O)=O)(O)=O)(O)=O)O3

⚫ | MeSHName=adenosine+thiamine+triphosphate
| UNII = 9FE2NX8HJW
⚫ | CASNo_Comment = (chloride)
⚫ | PubChem = 15938962
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 71394
⚫ | SMILES = NC1=NC=NC2=C1N=CN23(O)(O)(COP(OP(OP(OCCC4=C(C)(CC5=CN=C(C)N=C5N)=CS4)(O)=O)(O)=O)(O)=O)O3
⚫ | MeSHName=adenosine+thiamine+triphosphate
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=22|H=31|N=9|O=13|P=3|S=1 | C=22|H=31|N=9|O=13|P=3|S=1
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}

'''Adenosine thiamine triphosphate''' ('''AThTP'''), or '''thiaminylated adenosine triphosphate''', is a natural ] ] ].<ref>{{cite journal |vauthors =Bettendorff L, Wirtzfeld B, Makarchikov AF |title=Discovery of a natural thiamine adenine nucleotide |journal=Nat. Chem. Biol. |volume=3 |issue=4 |pages=211–2 |year=2007 |pmid=17334376 |doi=10.1038/nchembio867|hdl=2268/518 |s2cid=28498198 |display-authors=etal|hdl-access=free }}</ref> It was discovered in '']'' where it may account for up to 15 - 20% of total thiamine under carbon starvation. AThTP also exists in ] organisms such as yeast, roots of higher plants and animal tissues, albeit at a much lower concentration. It was found to exist in small amounts in the muscle, heart, brain, kidneys and liver of mice.<ref name="Tanaka 2011"/>

In ''E. coli'' AThTP is synthesized from ] (ThDP) according to the following reaction catalyzed by ]:<ref>{{cite journal |vauthors =Makarchikov AF, Brans A, Bettendorff L |name-list-style =amp |title=Thiamine diphosphate adenylyl transferase from E. coli: functional characterization of the enzyme synthesizing adenosine thiamine triphosphate |journal=BMC Biochem. |volume=8 |year=2007 |pmid=17705845 |doi=10.1186/1471-2091-8-17 |pages=17 |pmc=1976097 |doi-access =free }}</ref>

:ThDP + ATP (ADP) ↔ AThTP + PP<sub>i</sub> (P<sub>i</sub>)

==Structure and function==

The molecule is made up of thiamine and adenosine joined together with phosphate groups. It is similar in structure to NAD+. The function of AThTP is not currently known but it has been shown to inhibit the activity of PARP-1.<ref name="Tanaka 2011">{{cite journal|title=Adenosine thiamine triphosphate (AThTP) inhibits poly(ADP-ribose) polymerase-1(PARP-1) activity|vauthors =Tanaka T, Yamamoto D, Sato T, Tanaka S, Usui K, Manabe M, Aoki Y, Iwashima Y, Saito Y, Mino Y, Deguchi H|journal=J Nutr Sci Vitaminol (Tokyo)|year=2011|volume=57|issue=2|pages=192–6|pmid= 21697640|doi =10.3177/jnsv.57.192|doi-access=free}}</ref>

== References==
{{reflist}}

== External links ==
* {{cite journal |title=A first for vitamins |journal=Nature |volume=446 |issue=7132 |pages=112–113 |year=2007 |doi=10.1038/446112a |doi-access=free }}
* {{cite journal |author =Jordan F |title=Adenosine triphosphate and thiamine cross paths |journal=Nat. Chem. Biol. |volume=3 |issue=4 |pages=202–3 |year=2007 |pmid=17372602 |doi=10.1038/nchembio0407-202 }}

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