Structured Summary
Abstract
5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.
Chemical Identity
Chemical Information
- Molecular Formula
- C10H17N6O12P3
- Molecular Weight
- 506.20 g/mol
- CAS Registry No.
- 25612-73-1
- IUPAC Name
- [[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]amino]phosphonic acid
- InChIKey
- PVKSNHVPLWYQGJ-KQYNXXCUSA-N
- SMILES
- C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(NP(=O)(O)O)O)O)O)N
- MeSH Unique ID
- D000266
- Source
- PubChem CID 33113
MeSH Record
Classification
Broader headings
Related Concepts
Knowledge Graph
Drag nodes to rearrange; hover to trace links; click a node to open its page.
MeSH Record
Synonyms
20 entry terms
- AMP-PNP
- AMPPNP
- ATP(beta,gamma-NH)
- Adenosine 5'-(beta,gamma-Imino)triphosphate
- Adenyl Imidodiphosphate
- Adenylimidodiphosphate
- Adenylylimidodiphosphate
- beta,gamma-imido-ATP
- gamma-Imido-ATP
- gamma-Imino-ATP
- Imidodiphosphate, Adenyl
- Imidodiphosphate, Adenylyl
- beta,gamma imido ATP
- gamma Imido ATP
- gamma Imino ATP
- Mg AMP-PNP
- Mg-5'-Adenylylimidodiphosphate
- AMP-PNP, Mg
- Mg 5' Adenylylimidodiphosphate
- Mg AMP PNP
MeSH Record
Aspects Covered
29 allowable subheadings
Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, deficiency, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.
MeSH Record
History Note
91(76); was see under ADENOSINE TRIPHOSPHATE 1976-90
MeSH Record
Previous Indexing
- Adenosine Diphosphate (1973-1974)
- Adenosine Triphosphate/analogs & derivatives (1975)
- Imides (1973-1975)
- Phosphoric Acids (1973-1974)
MeSH Hierarchy
Tree Numbers
AMA Style
References
- National Library of Medicine. Adenylyl Imidodiphosphate. Medical Subject Headings (MeSH). 2026. Unique ID D000266. http://id.nlm.nih.gov/mesh/2026/D000266
- Adenylyl Imidodiphosphate. In: Wikidata. https://www.wikidata.org/wiki/Q15989037
- Adenylyl Imidodiphosphate. In: PubChem Compound. CID 33113. https://pubchem.ncbi.nlm.nih.gov/compound/33113