Showing Metabocard for GTP (BASm0002035)

Common Name

Gtp

Description

Guanosine-5'-triphosphate (GTP) is a purine nucleoside triphosphate. It is one of the building blocks needed for the synthesis of RNA during the transcription process. Its structure is similar to that of the guanosine nucleoside, the only difference being that nucleotides like GTP have phosphates on their ribose sugar. GTP has the guanine nucleobase attached to the 1' carbon of the ribose and it has the triphosphate moiety attached to ribose's 5' carbon. GTP is essential to signal transduction, in particular with G-proteins, in second-messenger mechanisms where it is converted to guanosine diphosphate (GDP) through the action of GTPases. Guanosine triphosphate, also known as 5'-GTP or H4GTP, belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribonucleotides with a triphosphate group linked to the ribose moiety. Thus, a GTP-bound tubulin serves as a cap at the tip of microtubule to protect from depolymerization; and, once the GTP is hydrolyzed, the microtubule begins to depolymerize and shrink rapidly. Guanosine triphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine triphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Guanosine-5'-triphosphate (GTP) is a purine nucleoside triphosphate. Outside of the human body, guanosine triphosphate has been detected, but not quantified in several different foods, such as mandarin orange (clementine, tangerine), coconuts, new zealand spinachs, sweet marjorams, and pepper (capsicum). Cyclic guanosine triphosphate (cGTP) helps cyclic adenosine monophosphate (cAMP) activate cyclic nucleotide-gated ion channels in the olfactory system. It also has the role of a source of energy or an activator of substrates in metabolic reactions, like that of ATP, but more specific. It is used as a source of energy for protein synthesis and gluconeogenesis. For instance, a GTP molecule is generated by one of the enzymes in the citric acid cycle. GTP is also used as an energy source for the translocation of the ribosome towards the 3' end of the mRNA. During microtubule polymerization, each heterodimer formed by an alpha and a beta tubulin molecule carries two GTP molecules, and the GTP is hydrolyzed to GDP when the tubulin dimers are added to the plus end of the growing microtubule. The importing of these proteins plays an important role in several pathways regulated within the mitochondria organelle, such as converting oxaloacetate to phosphoenolpyruvate (PEP) in gluconeogenesis. GTP is involved in energy transfer within the cell.

Structure

Molecular Formula

C₁₀H₁₆N₅O₁₄P₃

Average Mass

523.18040

Monoisotopic Mass

522.99066

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](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}oxy(hydroxy)phosphoryl)oxyphosphonic acid

CAS Registry Number

86-01-1

SMILES

Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1

InChI Identifier

InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1

InChI Key

XKMLYUALXHKNFT-UUOKFMHZSA-N

CHEBI ID

CHEBI:37565

HMDB ID

HMDB0001273

Pathways

Name	SMPDB/PathBank
Purine metabolism
Fructose and mannose metabolism
Pyruvate metabolism
Pterine Biosynthesis
Transcription/Translation
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)
Azithromycin Action Pathway
Clarithromycin Action Pathway
Clindamycin Action Pathway
Erythromycin Action Pathway
Roxithromycin Action Pathway
Telithromycin Action Pathway
Amikacin Action Pathway
Gentamicin Action Pathway
Kanamycin Action Pathway
Neomycin Action Pathway
Netilmicin Action Pathway
Spectinomycin Action Pathway
Streptomycin Action Pathway
Clomocycline Action Pathway
Demeclocycline Action Pathway
Doxycycline Action Pathway
Minocycline Action Pathway
Oxytetracycline Action Pathway
Tetracycline Action Pathway
Lymecycline Action Pathway
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
DNA Replication Fork
Dopa-responsive dystonia
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)
Hyperphenylalaninemia due to dhpr-deficiency
Segawa syndrome
Sepiapterin reductase deficiency
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)
Fructosuria
Fructose-1,6-diphosphatase deficiency
Triosephosphate isomerase
Glycogenosis, Type IB
Glycogenosis, Type IC
Glycogenosis, Type IA. Von gierke disease
Warburg Effect
Tobramycin Action Pathway
Tigecycline Action Pathway
Arbekacin Action Pathway
Paromomycin Action Pathway
Fructose intolerance, hereditary
Rolitetracycline Action Pathway
Methacycline Action Pathway
Lincomycin Action Pathway
Chloramphenicol Action Pathway
Troleandomycin Action Pathway
Josamycin Action Pathway
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

State

Solid

Water Solubility

1.04e+01 g/l

logP

-0.63

logS

-1.70

pKa (Strongest Acidic)

0.80

pKa (Strongest Basic)

1.57

Hydrogen Acceptor Count

Hydrogen Donor Count

Polar Surface Area

294.81 Å²

Rotatable Bond Count

Physiological Charge

-3

Formal Charge

Refractivity

97.24 m³·mol⁻¹

Polarizability

39.81

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