adenosine diphosphate

Also known as ADP, 5'-adenylphosphoric acid, H3adp, [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxyphosphonic acid, [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxyphosphonic acid, Adenosine-diphosphate, [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

chemical compound

OverviewAI-generated

Adenosine diphosphate is a chemical compound with the formula C₁₀H₁₅N₅O₁₀P₂. Its mass is listed as 427.029, while its weight is recorded as 427.20. The substance has a charge of 0 and an xlogp value of -4.6. It contains 6 hydrogen bond donors and 14 hydrogen bond acceptors, with a topological polar surface area of 233.

The compound is associated with a PubMed query count of 40178. It is referenced by 899 other encyclopedia articles.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C10H15N5O10P2
Molecular weight: 427.2 g/mol
IUPAC name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O)O)O)N
InChIKey: XTWYTFMLZFPYCI-KQYNXXCUSA-N
XLogP: -4.6
Polar surface area: 233 Å²
H-bond donors: 6
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

40,178 papers

Poly(adenosine diphosphate ribose).Progress in nucleic acid research and molecular biology · 1973
4-Thioribose Analogues of Adenosine Diphosphate Ribose (ADPr) Peptides.Organic letters · 2023
Adenosine diphosphate as a mediator of platelet aggregation in vivo.Advances in experimental medicine and biology · 1985
Accumulation of poly (adenosine diphosphate-ribose) by sustained supply of calcium inducing mitochondrial stress in pancreatic cancer cells.World journal of gastroenterology · 2022
Perioperative management of patients on adenosine diphosphate inhibitors in the era of drug-eluting stents: review of the literature and clinical implications.Current medicinal chemistry · 2009

via PubMed

Wikidata facts

Subclass of: coenzymes
Has part: carbon
Mass: 427.029

Show 5 more facts

chemical formula: C₁₀H₁₅N₅O₁₀P₂
isomeric SMILES: C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O)O)O
canonical SMILES: C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)OP(=O)(O)O)O)O
found in taxon: Caenorhabditis elegans
Commons category: Adenosine diphosphate

Sources (4)

via Wikidata · CC0

~7 min read

Encyclopedic overview

Adenosine diphosphate (ADP), also known as adenosine pyrophosphate (APP), is an important organic compound in metabolism and is essential to the flow of energy in living cells. ADP consists of three important structural components: a sugar backbone attached to adenine and two phosphate groups bonded to the 5-carbon atom of ribose. The diphosphate group of ADP is attached to the 5' carbon of the sugar backbone, while the adenine attaches to the 1' carbon.

ADP can be interconverted to adenosine triphosphate (ATP) and adenosine monophosphate (AMP). ATP contains one more phosphate group than ADP, while AMP contains one fewer phosphate group. Energy transfer used by all living things is a result of dephosphorylation of ATP by enzymes known as ATPases. The cleavage of a phosphate group from ATP results in the coupling of energy to metabolic reactions and a by-product of ADP. ATP is continually reformed from lower-energy species ADP and AMP. The biosynthesis of ATP is achieved throughout processes such as substrate-level phosphorylation, oxidative phosphorylation, and photophosphorylation, all of which facilitate the addition of a phosphate group to ADP.

Excerpted from Wikipedia’s “adenosine diphosphate” article, available under the CC BY-SA 4.0 licence.