| Record Information |
|---|
| Version | 3.6 |
|---|
| Creation Date | 2005-11-16 15:48:42 UTC |
|---|
| Update Date | 2017-03-02 21:26:25 UTC |
|---|
| HMDB ID | HMDB01178 |
|---|
| Secondary Accession Numbers | None |
|---|
| Metabolite Identification |
|---|
| Common Name | Adenosine diphosphate ribose |
|---|
| Description | Adenosine diphosphate ribose is a molecule formed into poly(ADP-ribose) or PAR chains by the enzyme poly ADP ribose polymerase or PARP. PARP is found in every cell nucleus. Its main role is to detect and signal single-strand DNA breaks (SSB) to the enzymatic machinery involved in the SSB repair. PARP activation is an immediate cellular response to metabolic, chemical, or radiation-induced DNA SSB damage. Once PARP detects a SSB, it binds to the DNA, and, after a structural change, begins the synthesis of a poly (ADP-ribose) chain (PAR) as a signal for the other DNA-repairing enzymes such as DNA ligase III (LigIII), DNA polymerase beta, and scaffolding proteins such as X-ray cross-complementing gene 1 (XRCC1). After repairing, the PAR chains are degraded via PAR glycohydrolase (PARG). ADP-ribose binds to and activates the TRPM2 ion channel. Adenosine diphosphate ribose is an intermediate in NAD metabolism. The enzyme NAD(P)+ nucleosidase [EC:3.2.2.6] catalyzes the production of this metabolite from nicotinamide adenine dinucleotide phosphate. This reaction is irreversible and occurs in the cytosol. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (Rib5)ppa | HMDB | | 5-(Adenosine 5'-pyrophosphoryl)-D-ribose | HMDB | | a5'pp5RIb | HMDB | | Adenosine 5'-diphosphoribose | HMDB | | AdoPPRib | HMDB | | ADP Ribose | HMDB | | ADP-D-Ribose | HMDB | | ADP-Rib | HMDB | | ADP-Ribose | HMDB | | ADPribose | HMDB | | D-Ribofuranos-5-yl-ADP | HMDB | | Ribose adenosine diphosphate | HMDB | | [5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl] hydrogen phosphate | HMDB | | Diphosphate ribose, adenosine | MeSH | | 5'-Diphosphoribose, adenosine | MeSH | | Adenosine diphosphoribose | MeSH | | Diphosphoribose, adenosine | MeSH | | Adenosine 5' diphosphoribose | MeSH | | Ribose, ADP | MeSH | | Ribose, adenosine diphosphate | MeSH |
|
|---|
| Chemical Formula | C15H23N5O14P2 |
|---|
| Average Molecular Weight | 559.3157 |
|---|
| Monoisotopic Molecular Weight | 559.071673493 |
|---|
| IUPAC Name | {[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl}oxy)phosphinic acid |
|---|
| Traditional Name | adp ribose |
|---|
| CAS Registry Number | 20762-30-5 |
|---|
| SMILES | NC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(O)C(O)C4O)C(O)C3O)C2=NC=N1 |
|---|
| InChI Identifier | InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18) |
|---|
| InChI Key | SRNWOUGRCWSEMX-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | This compound belongs to the class of chemical entities known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
|---|
| Kingdom | Chemical entities |
|---|
| Super Class | Organic compounds |
|---|
| Class | Nucleosides, nucleotides, and analogues |
|---|
| Sub Class | Purine nucleotides |
|---|
| Direct Parent | Purine nucleotide sugars |
|---|
| Alternative Parents | |
|---|
| Substituents | - Purine nucleotide sugar
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Primary aromatic amine
- Imidolactam
- Alkyl phosphate
- Pyrimidine
- Oxolane
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Hemiacetal
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Polyol
- Organic oxide
- Hydrocarbon derivative
- Organic nitrogen compound
- Alcohol
- Organic oxygen compound
- Amine
- Primary amine
- Organonitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
| Status | Expected but not Quantified |
|---|
| Origin | |
|---|
| Biofunction | - Component of nicotinate and nicotinamide metabolism
- Component of purine metabolism
- Second messenger
|
|---|
| Application | Not Available |
|---|
| Cellular locations | - Cytoplasm
- Extracellular
- Mitochondria
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| General References | - Hardie WD, Wright PE, Bernard GR: Effects of intravenous amphotericin B infusion on hemodynamics and airway mechanics in awake sheep. Chest. 1991 Feb;99(2):457-62. [PubMed:1989809 ]
- Garcia-Szabo R, Kern DF, Malik AB: Pulmonary vascular response to thrombin: effects of thromboxane synthetase inhibition with OKY-046 and OKY-1581. Prostaglandins. 1984 Dec;28(6):851-66. [PubMed:6543018 ]
- Vela-Navarrete R, Escribano-Burgos M, Farre AL, Garcia-Cardoso J, Manzarbeitia F, Carrasco C: Serenoa repens treatment modifies bax/bcl-2 index expression and caspase-3 activity in prostatic tissue from patients with benign prostatic hyperplasia. J Urol. 2005 Feb;173(2):507-10. [PubMed:15643230 ]
|
|---|
