Showing Metabocard for GDP (BASm0003270)

Common NameGdp
DescriptionGuanosine diphosphate, also known as 5'-GDP or 5'-diphosphate, guanosine, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine diphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Outside of the human body, Guanosine diphosphate has been detected, but not quantified in several different foods, such as devilfish, java plums, green beans, almonds, and orange mints. Guanosine diphosphate is a purine ribonucleoside 5'-diphosphate resulting from the formal condensation of the hydroxy group at the 5' position of guanosine with pyrophosphoric acid.
Structure
Molecular FormulaC10H15N5O11P2
Average Mass443.20050
Monoisotopic Mass443.02433
IUPAC Name[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2r,3s,4r,5r)-5-(2-amino-6-oxo-1h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number146-91-8
SMILESNc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1
InChI IdentifierInChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
InChI KeyQGWNDRXFNXRZMB-UUOKFMHZSA-N
CHEBI IDCHEBI:58189
HMDB IDHMDB0001201
Pathways
NameSMPDB/PathBank
Purine metabolism
Pyruvate metabolism
Citric Acid Cycle
Aspartate Metabolism
Gluconeogenesis
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Canavan Disease
Hypoacetylaspartia
Leigh Syndrome
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Pyruvate Dehydrogenase Complex Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Dopamine Activation of Neurological Reward System
Excitatory Neural Signalling Through 5-HTR 4 and Serotonin
Corticotropin Activation of Cortisol Production
Excitatory Neural Signalling Through 5-HTR 7 and Serotonin
Excitatory Neural Signalling Through 5-HTR 6 and Serotonin
Intracellular Signalling Through Adenosine Receptor A2a and Adenosine
Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
Vasopressin Regulation of Water Homeostasis
Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Intracellular Signalling Through Histamine H2 Receptor and Histamine
Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin
Intracellular Signalling Through PGD2 receptor and Prostaglandin D2
Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease
Insulin Signalling
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
Activation of PKC through G protein coupled receptor
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
Histamine H1 Receptor Activation
Chlorphenamine H1-Antihistamine Action
Pheniramine H1-Antihistamine Action
Dexchlorpheniramine H1-Antihistamine Action
Brompheniramine H1-Antihistamine Action
Dexbrompheniramine H1-Antihistamine Action
Triprolidine H1-Antihistamine Action
Dimetindene H1-Antihistamine Action
Mepyramine H1-Antihistamine Action
Antazoline H1-Antihistamine Action
Chloropyramine H1-Antihistamine Action
Talastine H1-Antihistamine Action
Tripelennamine H1-Antihistamine Action
Histapyrrodine H1-Antihistamine Action
Methapyrilene H1-Antihistamine Action
Thonzylamine H1-Antihistamine Action
Diphenhydramine H1-Antihistamine Action
Carbinoxamine H1-Antihistamine Action
Doxylamine H1-Antihistamine Action
Orphenadrine H1-Antihistamine Action
Bromodiphenhydramine H1-Antihistamine Action
Clemastine H1-Antihistamine Action
Chlorphenoxamine H1-Antihistamine Action
Diphenylpyraline H1-Antihistamine Action
Phenyltoloxamine H1-Antihistamine Action
Cyclizine H1-Antihistamine Action
Chlorcyclizine H1-Antihistamine Action
Hydroxyzine H1-Antihistamine Action
Meclizine H1-Antihistamine Action
Buclizine H1-Antihistamine Action
Oxatomide H1-Antihistamine Action
Cetirizine H1-Antihistamine Action
Cinnarizine H1-Antihistamine Action
Levocetirizine H1-Antihistamine Action
Promethazine H1-Antihistamine Action
Alimemazine H1-Antihistamine Action
Cyproheptadine H1-Antihistamine Action
Phenbenzamine H1-Antihistamine Action
Fenethazine H1-Antihistamine Action
Hydroxyethylpromethazine H1-Antihistamine Action
Isothipendyl H1-Antihistamine Action
Mequitazine H1-Antihistamine Action
Methdilazine H1-Antihistamine Action
Oxomemazine H1-Antihistamine Action
Azatadine H1-Antihistamine Action
Ketotifen H1-Antihistamine Action
Doxepin H1-Antihistamine Action
Acrivastine H1-Antihistamine Action
Astemizole H1-Antihistamine Action
Bepotastine H1-Antihistamine Action
Bilastine H1-Antihistamine Action
Loratadine H1-Antihistamine Action
Desloratadine H1-Antihistamine Action
Ebastine H1-Antihistamine Action
Terfenadine H1-Antihistamine Action
Fexofenadine H1-Antihistamine Action
Levocabastine H1-Antihistamine Action
Mizolastine H1-Antihistamine Action
Rupatadine H1-Antihistamine Action
Olopatadine H1-Antihistamine Action
Azelastine H1-Antihistamine Action
Thiazinamium H1-Antihistamine Action
Quifenadine H1-Antihistamine Action
Betahistine H1-Antihistamine Action
Emedastine H1-Antihistamine Action
Flunarizine H1-Antihistamine Action
Mebhydrolin H1-Antihistamine Action
Phenindamine H1-Antihistamine Action
Epinastine H1-Antihistamine Action
Tolpropamine H1-Antihistamine Action
Embramine H1-Antihistamine Action
Latrepirdine H1-Antihistamine Action
Thenyldiamine H1-Antihistamine Action
Propiomazine H1-Antihistamine Action
Clocinizine H1-Antihistamine Action
Homochlorcyclizine H1-Antihistamine Action
Temelastine H1-Antihistamine Action
Alcaftadine H1-Antihistamine Action
Bamipine H1-Antihistamine Action
Deptropine H1-Antihistamine Action
Quetiapine H1-Antihistamine Action
Mirtazapine H1-Antihistamine Action
Pimethixene H1-Antihistamine Action
Pyrrobutamine H1-Antihistamine Action
Thenalidine H1-Antihistamine Action
Tritoqualine H1-Antihistamine Action
Histamine H1 Receptor Activation
Lysophosphatidic Acid LPA1 Signalling
Lysophosphatidic Acid LPA2 Signalling
Lysophosphatidic Acid LPA3 Signalling
Lysophosphatidic Acid LPA4 Signalling
Lysophosphatidic Acid LPA5 Signalling
Lysophosphatidic Acid LPA6 Signalling
StateSolid
Water Solubility4.44e+00 g/l
logP-1.51
logS-2.00
pKa (Strongest Acidic)1.97
pKa (Strongest Basic)1.35
Hydrogen Acceptor Count12
Hydrogen Donor Count7
Polar Surface Area248.28 Ų
Rotatable Bond Count6
Physiological Charge-2
Formal Charge0
Refractivity86.37 m³·mol⁻¹
Polarizability35.28

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