Np mrd loader

Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:04 UTC
NP-MRD IDNP0000794
Secondary Accession NumbersNone
Natural Product Identification
Common NamedGTP
DescriptionDeoxyguanosine triphosphate (dGTP) is a nucleoside triphosphate, and a nucleotide precursor used in cells for DNA synthesis. DGTP is used in the polymerase chain reaction technique, in sequencing, and in cloning. It is also the competitor of inhibition onset by acyclovir in the treatment of HSV virus. Under normal physiologic conditions, deoxyguanosine (dGuo) undergoes phosphorolysis by purine nucleoside phosphorylase (PNP, EC 2.4.2.1, An enzyme involved in the recycling of nucleosides and deoxynucleosides in cellular remodeling). However, when PNP is inhibited, deoxycytidine kinase (dCK, EC 2.7.1.74) Shunts unmetabolized dGuo into deoxyguanosine triphosphate (dGTP), which accumulates and blocks DNA synthesis. Deficiency of purine nucleoside phosphorylase results in defective T-cell immunity. A correlation between the degree of T cell inhibition and the level of dCK activity has been observed. (PMID: 11287638 , 402573 ).
Structure
Thumb
Synonyms
ValueSource
2'-Deoxy-GTPChEBI
2'-Deoxyguanosine 5'-triphosphateChEBI
2'-Deoxyguanosine triphosphateChEBI
Deoxy-GTPChEBI
Deoxyguanosine 5'-triphosphateChEBI
Deoxyguanosine triphosphateChEBI
2'-Deoxyguanosine 5'-triphosphoric acidGenerator
2'-Deoxyguanosine triphosphoric acidGenerator
Deoxyguanosine 5'-triphosphoric acidGenerator
Deoxyguanosine triphosphoric acidGenerator
Deoxyguanosine triphosphate, 3H-labeledHMDB
Chemical FormulaC10H16N5O13P3
Average Mass507.1810 Da
Monoisotopic Mass506.99575 Da
IUPAC Name({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional NamedGTP
CAS Registry Number2564-35-4
SMILES
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1
InChI Identifier
InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
InChI KeyHAAZLUGHYHWQIW-KVQBGUIXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.59 g/LALOGPS
logP-0.61ALOGPS
logP-3.2ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)0.33ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area274.58 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.73 m³·mol⁻¹ChemAxon
Polarizability39.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0001440
DrugBank IDDB02181
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022623
KNApSAcK IDC00019346
Chemspider ID58613
KEGG Compound IDC00286
BioCyc IDDGTP
BiGG ID34502
Wikipedia LinkDeoxyguanosine_triphosphate
METLIN ID6248
PubChem Compound65103
PDB IDNot Available
ChEBI ID16497
Good Scents IDNot Available
References
General References
  1. Kicska GA, Long L, Horig H, Fairchild C, Tyler PC, Furneaux RH, Schramm VL, Kaufman HL: Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes. Proc Natl Acad Sci U S A. 2001 Apr 10;98(8):4593-8. Epub 2001 Apr 3. [PubMed:11287638 ]
  2. Stoop JW, Zegers BJ, Hendrickx GF, van Heukelom LH, Staal GE, de Bree PK, Wadman SK, Ballieux RE: Purine nucleoside phosphorylase deficiency associated with selective cellular immunodeficiency. N Engl J Med. 1977 Mar 24;296(12):651-5. [PubMed:402573 ]
  3. Hardy CD, Schultz CS, Collins K: Requirements for the dGTP-dependent repeat addition processivity of recombinant Tetrahymena telomerase. J Biol Chem. 2001 Feb 16;276(7):4863-71. doi: 10.1074/jbc.M005158200. Epub 2000 Nov 28. [PubMed:11096070 ]
  4. Torti A, Lossani A, Savi L, Focher F, Wright GE, Brown NC, Xu WC: Clostridium difficile DNA polymerase IIIC: basis for activity of antibacterial compounds. Curr Enzym Inhib. 2011 Oct;7(3):147-153. doi: 10.2174/157340811798807597. [PubMed:22844265 ]
  5. Muller EG: Deoxyribonucleotides are maintained at normal levels in a yeast thioredoxin mutant defective in DNA synthesis. J Biol Chem. 1994 Sep 30;269(39):24466-71. [PubMed:7929110 ]