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Human Metabolome Database Version 3.5

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Showing metabocard for Guanosine diphosphate adenosine (HMDB01501)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:40 -0700
HMDB ID HMDB01501
Secondary Accession Numbers None
Metabolite Identification
Common Name Guanosine diphosphate adenosine
Description Guanosine diphosphate 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
    Chemical Formula C20H26N10O14P2
    Average Molecular Weight 692.4266
    Monoisotopic Molecular Weight 692.110518614
    IUPAC Name {[(2R,3R,4R,5R)-4-[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
    Traditional IUPAC Name [(2R,3R,4R,5R)-4-({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid
    CAS Registry Number 65331-78-4
    SMILES NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
    InChI Identifier InChI=1S/C20H26N10O14P2/c21-14-8-15(24-3-23-14)29(4-25-8)19-13(43-45(35,36)37)12(6(1-31)41-19)44-46(38,39)40-2-7-10(32)11(33)18(42-7)30-5-26-9-16(30)27-20(22)28-17(9)34/h3-7,10-13,18-19,31-33H,1-2H2,(H,38,39)(H2,21,23,24)(H2,35,36,37)(H3,22,27,28,34)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
    InChI Key LHSVDZHIRYSVJP-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
    • Oxolane
    • Pentose Disaccharide
    • Phosphoric Acid Ester
    • Polyamine
    • Primary Alcohol
    • Purine
    • Purinone
    • Pyrimidine
    • Pyrimidone
    • Saccharide
    • Secondary Alcohol
    Direct Parent Purine Ribonucleoside Monophosphates
    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 4.67 g/L ALOGPS
    LogP -1.46 ALOGPS
    LogP -7.2 ChemAxon
    LogS -2.17 ALOGPS
    pKa (strongest acidic) 0.47 ChemAxon
    pKa (strongest basic) 4.87 ChemAxon
    Hydrogen Acceptor Count 19 ChemAxon
    Hydrogen Donor Count 9 ChemAxon
    Polar Surface Area 356.59 A2 ChemAxon
    Rotatable Bond Count 10 ChemAxon
    Refractivity 145.35 ChemAxon
    Polarizability 58.47 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
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022659
    KNApSAcK ID Not Available
    Chemspider ID 8637730 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB01501 Link_out
    Metagene Link HMDB01501 Link_out
    METLIN ID Not Available
    PubChem Compound 10462318 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References Not Available