Guanosine pentaphosphate

Guanosine pentaphosphate
Names
	Other names guanosine pentaphosphate (pppGpp), guanosine tetraphosphate (ppGpp)
Identifiers
CAS Number	tetraphosphate: 32452-17-8; pentaphosphate: 38918-96-6;
3D model (JSmol)	tetraphosphate: Interactive image; pentaphosphate: Interactive image;
Beilstein Reference	(pentaphosphate) 1205996
ChEBI	tetraphosphate: CHEBI:17633; pentaphosphate: CHEBI:16690;
ChemSpider	tetraphosphate: 388557; pentaphosphate: 34987;
DrugBank	tetraphosphate: DB04022;
KEGG	tetraphosphate: C01228; pentaphosphate: C04494;
PubChem CID	tetraphosphate: 135398637; pentaphosphate: 135398629;
CompTox Dashboard (EPA)	pentaphosphate: DTXSID50955132;
	InChI tetraphosphate: InChI=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 Key: BUFLLCUFNHESEH-UUOKFMHZSA-N; pentaphosphate: InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 Key: KCPMACXZAITQAX-UUOKFMHZSA-N;
	SMILES tetraphosphate: O[C@H]1[C@H](N2C3=C(N=C2)C(=O)N=C(N)N3)O[C@H](COP(OP(=O)(O)O)(=O)O)[C@H]1OP(OP(=O)(O)O)(=O)O; pentaphosphate: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)OP(=O)(O)OP(=O)(O)O)O)N=C(NC2=O)N;
Properties
Chemical formula	C10H18N5O20P5
Molar mass	683.14 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

(p)ppGpp, guanosine pentaphosphate and tetraphosphate, also known as the "magic spot" nucleotides, are alarmones involved in the stringent response in bacteria that cause the inhibition of RNA synthesis when there is a shortage of amino acids. This inhibition by (p)ppGpp decreases translation in the cell, conserving amino acids present. Furthermore, ppGpp and pppGpp cause the up-regulation of many other genes involved in stress response such as the genes for amino acid uptake (from surrounding media) and biosynthesis. (p)ppGpp is also conserved in plants, where it is known to play a role in regulating growth and developmental processes.