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Human Metabolome Database Version 3.5

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Showing metabocard for Diadenosine diphosphate (HMDB01312)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:31:10 -0600
HMDB ID HMDB01312
Secondary Accession Numbers None
Metabolite Identification
Common Name Diadenosine diphosphate
Description Diadenosine diphosphate is a member of the diadenosine polyphosphates. Diadenosine diphosphate is typically synthesized from ADP-ribosyl cyclases. Diadenosine polyphosphates are members of a group of dinucleoside polyphosphates that are ubiquitous, naturally occurring molecules. They form a recently identified class of compounds derived from ATP and consist of two adenosine molecules bridged by up to six phosphate groups. These compounds are stored in high concentrations in platelet dense granules and are released when platelets become activated. Some of the compounds promote platelet aggregation, while others are inhibitory. Possible roles as neurotransmitters, extracellular signalling molecules or 'alarmones' secreted by cells in response to physiologically stressful stimuli have been postulated. Recent studies suggest a role for these compounds in atrial and synaptic neurotransmission. Studies using isolated mesenteric arteries indicate an important role of phosphate chain length in determining whether diadenosine polyphosphates produce vasodilatation or vasoconstriction, but in the coronary circulation, diadenosine polyphosphates generally produce vasodilatation via mechanisms thought to involve release of NO or prostacyclin (PGI2). They produce cardiac electrophysiological effects by altering ventricular refractoriness at submicromolar concentrations and reduce heart rate. Mechanisms involving KATP channels have been proposed in addition to the involvement of P1- and P2-purinergic receptors and the specific diadenosine polyphosphate receptor identified on isolated cardiac myocytes. Clinical evidence suggests a role for diadenosine polyphosphates in hypertensive patients and those with the Chediak-Higashi syndrome. (PMID: 10434992 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Diadenosine pyrophosphate
  2. Diadenosine-5',5'-pyrophosphate
  3. P(1),P(2)-Di(adenosine 5'-)diphosphate
  4. P(1),P(2)-Diadenosine-5'-pyrophosphate
Chemical Formula C20H26N10O13P2
Average Molecular Weight 676.4272
Monoisotopic Molecular Weight 676.115603992
IUPAC Name [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy})phosphinic acid
Traditional IUPAC Name {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2R,3S,4R,5S)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyphosphinic acid
CAS Registry Number 14938-28-4
SMILES NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1
InChI Identifier InChI=1S/C20H26N10O13P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(33)11(32)8(41-19)2-39-44(35,36)43-45(37,38)42-14-7(1-31)40-20(13(14)34)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20+/m1/s1
InChI Key FHISWBUCBBVWGG-SNESVTBZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Disaccharide
  • Phosphoric Acid Ester
  • Polyamine
  • Primary Alcohol
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
Direct Parent Purine Ribonucleoside Diphosphates
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
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
Property Value Source
Water Solubility 4.5 g/L ALOGPS
LogP -1.76 ALOGPS
LogP -8 ChemAxon
LogS -2.18 ALOGPS
pKa (strongest acidic) 1.84 ChemAxon
pKa (strongest basic) 5.29 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 340.91 A2 ChemAxon
Rotatable Bond Count 10 ChemAxon
Refractivity 144.36 ChemAxon
Polarizability 58.41 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022547
KNApSAcK ID Not Available
Chemspider ID 163689 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01312 Link_out
Metagene Link HMDB01312 Link_out
METLIN ID Not Available
PubChem Compound 188326 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Flores NA, Stavrou BM, Sheridan DJ: The effects of diadenosine polyphosphates on the cardiovascular system. Cardiovasc Res. 1999 Apr;42(1):15-26. Pubmed: 10434992 Link_out