Back سیکلیک ای دی پی-ریبوز AZB Difosfat d'adenosina de ribosa cíclic Catalan سیکلیک ای دی پی-ریبوز Persian Adénosine diphosphate ribose cyclique French ADP-ribosa cíclico Galician 環状アデノシン二リン酸リボース Japanese Cyclisch ADP-ribose Dutch Циклическая АДФ-рибоза Russian Ciklična ADP-riboza Serbo-Croatian Cyklická ADP-ribóza Slovak

Cyclic ADP-ribose

Cyclic ADP-ribose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.162.252 Edit this at Wikidata
MeSH Cyclic+ADP-Ribose
UNII
  • InChI=1S/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1 ☒N
    Key: BQOHYSXSASDCEA-KEOHHSTQSA-N ☒N
  • InChI=1/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
    Key: BQOHYSXSASDCEA-KEOHHSTQBN
  • O[C@H]5[C@@H](O)[C@H]2O[C@@H]5COP(O)(=O)OP(O)(=O)OC[C@H]4O[C@@H](N3\C=N/c1c(ncn12)C3=N)[C@H](O)[C@@H]4O
Properties
C15H21N5O13P2
Molar mass 541.301
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclic ADP-ribose, frequently abbreviated as cADPR, is a cyclic adenine nucleotide (like cAMP) with two phosphate groups present on 5' OH of the adenosine (like ADP), further connected to another ribose at the 5' position, which, in turn, closes the cycle by glycosidic bonding to the nitrogen 1 (N1) of the same adenine base (whose position N9 has the glycosidic bond to the other ribose).[1][2] The N1-glycosidic bond to adenine is what distinguishes cADPR from ADP-ribose (ADPR), the non-cyclic analog. cADPR is produced from nicotinamide adenine dinucleotide (NAD+) by ADP-ribosyl cyclases (EC 3.2.2.5) as part of a second messenger system.

  1. ^ Lee HC, Walseth TF, Bratt GT, Hayes RN, Clapper DL (1989). "Structural determination of a cyclic metabolite of NAD+ with intracellular Ca2+-mobilizing activity". J. Biol. Chem. 264 (3): 1608–15. doi:10.1016/S0021-9258(18)94230-4. PMID 2912976.
  2. ^ Lee HC, Aarhus R, Levitt D (1994). "The crystal structure of cyclic ADP-ribose". Nat. Struct. Biol. 1 (3): 143–4. doi:10.1038/nsb0394-143. PMID 7656029. S2CID 9049850.

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