Adenosine diphosphate ribose: Difference between revisions
Appearance
Content deleted Content added
Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo'). |
Citation bot (talk | contribs) Add: pmc, pmid, pages, issue, volume, journal, date, title, authors 1-6. | Use this bot. Report bugs. | Suggested by Marbletan | #UCB_webform |
||
(38 intermediate revisions by 27 users not shown) | |||
Line 1: | Line 1: | ||
{{chembox |
{{chembox |
||
| Verifiedfields = changed |
|||
⚫ | |||
| Watchedfields = changed |
|||
|ImageFile2=Adenosine diphosphate ribose 3D.png |
|||
| verifiedrevid = 457804269 |
|||
⚫ | |||
⚫ | |||
⚫ | |||
| ImageFile1=ADP-ribose 3D.png |
|||
⚫ | |||
| |
| ImageFile2=Three-dimensional model of ADP ribose.png |
||
⚫ | |||
⚫ | |||
⚫ | |||
| CASNo = <!-- blanked - oldvalue: 20762-30-5 --> |
|||
⚫ | |||
⚫ | |||
| OtherNames=ADP ribose<br/>ADPR<br />Adenosine 5'-diphosphoribose |
|||
| SMILES= |
|||
⚫ | |||
| ChEMBL = <!-- blanked - oldvalue: 1161865 --> |
|||
| CASNo_Ref = {{cascite|changed|??}} |
|||
⚫ | |||
| CASNo=20762-30-5 |
|||
| UNII_Ref = {{fdacite|correct|FDA}} |
|||
| UNII = XV3S4KV26E |
|||
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|||
| ChEMBL = 1161865 |
|||
⚫ | |||
⚫ | |||
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|||
| ChemSpiderID = 388340 |
|||
| SMILES = O=P(O[C@H]1O[C@H]([C@H](O)[C@@H]1O)CO)(O)OP(=O)(OC[C@H]4O[C@@H](n3c2ncnc(N)c2nc3)[C@H](O)[C@@H]4O)O |
|||
| InChI = 1/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(24)9(23)6(31-14)2-30-35(26,27)34-36(28,29)33-15-11(25)8(22)5(1-21)32-15/h3-6,8-11,14-15,21-25H,1-2H2,(H4,16,17,18,26,27,28,29)/p+1/t5-,6+,8-,9+,10+,11-,14+,15+/m0/s1 |
|||
| InChIKey = YNCNQNWXUFCWJS-LKOYDKQFBH |
|||
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|||
| StdInChI = 1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(24)9(23)6(31-14)2-30-35(26,27)34-36(28,29)33-15-11(25)8(22)5(1-21)32-15/h3-6,8-11,14-15,21-25H,1-2H2,(H4,16,17,18,26,27,28,29)/p+1/t5-,6+,8-,9+,10+,11-,14+,15+/m0/s1 |
|||
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|||
| StdInChIKey = YNCNQNWXUFCWJS-DKMYFHGXSA-O |
|||
}} |
}} |
||
|Section2= |
|Section2={{Chembox Properties |
||
| C=15 | H=23 | N=5 | O=14 | P=2 |
|||
| Formula=C<sub>15</sub>H<sub>23</sub>N<sub>5</sub>O<sub>14</sub>P<sub>2</sub> |
|||
| |
| MolarMass=559.316 g/mol |
||
| |
| Appearance= |
||
| |
| Density= |
||
| |
| MeltingPt= |
||
| |
| BoilingPt= |
||
| |
| Solubility= |
||
}} |
}} |
||
|Section3= |
|Section3={{Chembox Hazards |
||
| |
| MainHazards= |
||
| |
| FlashPt= |
||
| AutoignitionPt = |
|||
| Autoignition= |
|||
}} |
}} |
||
}} |
}} |
||
'''Adenosine diphosphate ribose''' is |
'''Adenosine diphosphate ribose''' ('''ADPR''') is an [[ester]] molecule formed into chains by the enzyme [[poly ADP ribose polymerase]].<ref name="pmid29634344">{{cite journal | vauthors = Braidy N, Berg J, Clement J, Sachdev P | title = Role of Nicotinamide Adenine Dinucleotide and Related Precursors as Therapeutic Targets for Age-Related Degenerative Diseases: Rationale, Biochemistry, Pharmacokinetics, and Outcomes | journal = [[Antioxidants & Redox Signaling]] | volume = 10 | issue = 2 | pages = 251–294 | date=2019 | doi = 10.1089/ars.2017.7269 | pmc =6277084 | pmid = 29634344}}</ref> ADPR is created from [[cyclic ADP-ribose]] (cADPR) by the [[CD38]] enzyme using [[nicotinamide adenine dinucleotide]] (NAD<sup>+</sup>) as a [[Cofactor (biochemistry)|cofactor]].<ref name="pmid29634344" /> |
||
ADPR binds to and activates the [[TRPM2]] ion channel.<ref name="pmid15302683">{{cite journal |vauthors =Fonfria E, Marshall IC, Benham CD |title=TRPM2 channel opening in response to oxidative stress is dependent on activation of poly(ADP-ribose) polymerase |journal=Br. J. Pharmacol. |volume=143 |issue=1 |pages=186–92 |date=September 2004|pmid=15302683 |pmc=1575275 |doi=10.1038/sj.bjp.0705914 |display-authors=etal}}</ref> ADPR is the most potent [[agonist]] of the TRPM2 channel.<ref name="pmid33092205">{{cite journal | vauthors = Yu P, Cai X, Liang Y, Yang W | title = Roles of NAD + and Its Metabolites Regulated Calcium Channels in Cancer | journal = [[Molecules]] | volume = 25 | issue = 20 | pages = 4826 | date=2019 | doi = 10.3390/molecules25204826 | pmc =7587972 | pmid = 33092205 | doi-access = free }}</ref> cADPR also binds to TPRM2, and the action of both molecules is [[Synergy|synergistic]], with both molecules enhancing the action of the other molecule in activating the TRPM2 channel.<ref name="pmid21786193">{{cite journal | author = Lee HC | title = Cyclic ADP-ribose and NAADP: fraternal twin messengers for calcium signaling | journal = Science China Life Sciences | volume = 54 | issue = 8 | pages = 699–711 | date=2011 | doi = 10.1007/s11427-011-4197-3 | pmid = 21786193| s2cid = 24286381 | doi-access = free }}</ref> Researchers are not sure how the Adenosine diphosphate reacts with the TRPM2 channel, but the ribose sugar may play a role in activating the [[TRPM2]] ion channel.<ref>{{cite journal | doi = 10.1021/acs.joc.9b00338 | title = Synthesis of Terminal Ribose Analogues of Adenosine 5′-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2 | date = 2019 | last1 = Baszczyňski | first1 = Ondřej | last2 = Watt | first2 = Joanna M. | last3 = Rozewitz | first3 = Monika D. | last4 = Guse | first4 = Andreas H. | last5 = Fliegert | first5 = Ralf | last6 = Potter | first6 = Barry V. L. | journal = The Journal of Organic Chemistry | volume = 84 | issue = 10 | pages = 6143–6157 | pmid = 30978018 | pmc = 6528165 }}</ref> |
|||
==See also== |
==See also== |
||
* [[Adenosine diphosphate]] |
* [[Adenosine diphosphate]] |
||
* [[ADP-ribosylation]] |
|||
* [[Ribose]] |
* [[Ribose]] |
||
* [[Poly (ADP-ribose) polymerase]] |
|||
==References== |
==References== |
||
{{ |
{{Reflist}} |
||
{{Transient receptor potential channel modulators}} |
|||
{{DEFAULTSORT:Adenosine Diphosphate Ribose}} |
{{DEFAULTSORT:Adenosine Diphosphate Ribose}} |
||
Line 42: | Line 64: | ||
[[Category:Organophosphates]] |
[[Category:Organophosphates]] |
||
[[Category:NADH dehydrogenase inhibitors]] |
[[Category:NADH dehydrogenase inhibitors]] |
||
[[Category:Phosphate esters]] |
|||
⚫ | |||
⚫ | |||
[[fr:Adénosine diphosphate ribose]] |
|||
[[it:Adenosina difosfato ribosio]] |