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Showing metabocard for Guanosine pentaphosphate adenosine (HMDB01472)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:37 -0700
HMDB ID HMDB01472
Secondary Accession Numbers None
Metabolite Identification
Common Name Guanosine pentaphosphate adenosine
Description Guanosine pentaphosphate adenosine is a dinucleoside polyphosphate. Dinucleoside polyphosphates are an interesting group of signalling molecules that control numerous physiological functions. Diadenosine compounds, with a backbone of anything from two to seven phosphates, are known to occur naturally. Some of them have been isolated from cerebral nerve terminals and, acting via nucleoside (P1), nucleotide (P2), or dinucleotide receptors, can affect central nervous system function. Many of them have been isolated from human blood platelet secretory granules and are potentially involved in haemostatic mechanisms and peripheral control of vascular tone. Many visceral organs respond to the application of adenine dinucleotides and, although they act on receptors in the periphery that can be mainly defined as either P1 or P2, evidence is now accumulating for discrete dinucleotide receptors. In the periphery, adenine dinucleotides can be potent agonists, with diverse functions, causing contraction or relaxation of smooth muscle. Many P2X receptor proteins and P2Y receptors have been cloned and adenine dinucleotides have a variable pharmacological profile at these receptors and may be useful tools for characterising subtypes of P2X and P2Y receptors. Many extracellular roles of diadenosine polyphosphates are emerging as yet increasingly important, natural ligands for a plethora of structurally diverse mononucleotide and dinucleotide receptors. (PMID: 12772275 Link_out, 7767329 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. P1-(5'-Adenosyl)-P5-(5'-guanosyl) pentaphosphate
Chemical Formula C20H29N10O23P5
Average Molecular Weight 932.3663
Monoisotopic Molecular Weight 932.009509844
IUPAC Name {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)phosphini
CAS Registry Number 56983-24-5
SMILES NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)O[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
InChI Identifier InChI=1S/C20H29N10O23P5/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(48-18)1-46-54(36,37)50-56(40,41)52-58(44,45)53-57(42,43)51-55(38,39)47-2-7-11(32)13(34)19(49-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChI Key CNMILLPGDWDFCZ-INFSMZHSSA-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
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Disaccharide
  • Phosphoric Acid Ester
  • Polyamine
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct Parent Purine Ribonucleoside Polyphosphates
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 8.95 g/L ALOGPS
LogP 0.11 ALOGPS
LogP -9.5 ChemAxon
LogS -2.02 ALOGPS
pKa (strongest acidic) 0.42 ChemAxon
pKa (strongest basic) 5 ChemAxon
Hydrogen Acceptor Count 25 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 496.18 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 177.97 ChemAxon
Polarizability 72.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022643
KNApSAcK ID Not Available
Chemspider ID 5254634 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01472 Link_out
Metagene Link HMDB01472 Link_out
METLIN ID Not Available
PubChem Compound 6852180 Link_out
PDB ID G5P Link_out
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available