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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:23:02 UTC |
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HMDB ID | HMDB0001178 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Adenosine diphosphate ribose |
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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. |
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Structure | |
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Synonyms | Value | Source |
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Adenosine diphosphoric acid ribose | Generator | (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 | HMDB | 5'-Diphosphoribose, adenosine | HMDB | Adenosine diphosphoribose | HMDB | Diphosphoribose, adenosine | HMDB | Adenosine 5' diphosphoribose | HMDB | Ribose, ADP | HMDB | Ribose, adenosine diphosphate | HMDB |
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Chemical Formula | C15H23N5O14P2 |
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Average Molecular Weight | 559.3157 |
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Monoisotopic Molecular Weight | 559.071673493 |
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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 |
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Traditional Name | adp ribose |
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CAS Registry Number | 20762-30-5 |
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SMILES | NC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(O)C(O)C4O)C(O)C3O)C2=NC=N1 |
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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) |
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InChI Key | SRNWOUGRCWSEMX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine nucleotide sugars |
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Direct Parent | Purine nucleotide sugars |
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Alternative Parents | |
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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
- Pyrimidine
- Alkyl phosphate
- Imidolactam
- Phosphoric acid ester
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Tetrahydrofuran
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Hemiacetal
- Organoheterocyclic compound
- Polyol
- Azacycle
- Oxacycle
- Organic oxide
- Amine
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Hydrocarbon derivative
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01r5-1196680000-fb6c20cc4fb54b50028e | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-01r5-2115904000-4597a65923641317c791 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0910130000-b9073b1bbcee0d4c7c6e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0910000000-4407a7719b31b18bb57b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-9d6c2b567f9da9d1d1ce | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a59-1701390000-e958d4521e35989750e1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1910100000-a653cbe7cba6b5fab234 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a7i-3900000000-c8a10ccf06e1cb8b548a | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondria
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022468 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 187 |
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KEGG Compound ID | C00301 |
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BioCyc ID | Not Available |
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BiGG ID | 34547 |
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Wikipedia Link | Adenosine diphosphate ribose |
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METLIN ID | 6059 |
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PubChem Compound | 192 |
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PDB ID | Not Available |
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ChEBI ID | 16960 |
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Food Biomarker Ontology | Not Available |
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VMH ID | ADPRIB |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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