G4P

GUANOSINE-5',3'-TETRAPHOSPHATE


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Chemical Component Summary

NameGUANOSINE-5',3'-TETRAPHOSPHATE
Synonymsguanosine tetraphosphate; ppGpp
Identifiers[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-4-hydroxy-3-(hydroxy-phosphonooxy-phosphoryl)oxy-oxolan-2-yl]methyl phosphono hydrogen phosphate
FormulaC10 H17 N5 O17 P4
Molecular Weight603.16
TypeRNA LINKING
Isomeric SMILESc1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)OP(=O)(O)O)O[P@](=O)(O)OP(=O)(O)O)O)N=C(NC2=O)N
InChIInChI=1S/C10H17N5O17P4/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(30-36(26,27)32-34(21,22)23)3(29-9)1-28-35(24,25)31-33(18,19)20/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
InChIKeyBUFLLCUFNHESEH-UUOKFMHZSA-N

Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count6
Bond Count55
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB04022 
NameGuanosine tetraphosphate
Groups experimental
DescriptionGuanosine tetraphosphate is a guanine nucleotide containing four phosphate groups. Two phosphate groups are esterified to the sugar moiety in the 5' position and the other two in the 2' or 3' position. This nucleotide serves as a messenger to turn off the synthesis of ribosomal RNA when amino acids are not available for protein synthesis.
Synonyms
  • Guanosine tetraphosphate
  • Guanosine-5',3'-tetraphosphate
Categories
  • Guanine Nucleotides
  • Heterocyclic Compounds, Fused-Ring
  • Nucleic Acids, Nucleotides, and Nucleosides
  • Nucleotides
  • Purine Nucleotides
CAS number33503-72-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Xanthine phosphoribosyltransferaseMEALKRKIEEEGVVLSDQVLKVDSFLNHQIDPLLMQRIGDEFASRFAKDG...unknown
GTPase ObgEMFVDQVKVYVKGGDGGNGMVAFRREKYVPKGGPAGGDGGKGGDVVFEVDE...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5280412, 439450, 135398637
ChEBI CHEBI:17633