Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:52:38 UTC
Update Date2024-04-30 19:44:30 UTC
Metabolite IDMMDBc0030066
Metabolite Identification
Common NameGuanosine 3'-diphosphate 5'-triphosphate
DescriptionGuanosine 3'-diphosphate 5'-triphosphate is a member of the chemical class known as Purine Ribonucleoside 3',5'-Bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. The hallmark of the stringent response is the accumulation of guanosine tetra- (ppGpp) and pentaphosphates (pppGpp), which probably bind RNA polymerase to regulate gene expression at certain promoters. (PMID 11282471 ) Guanosine 5'-triphosphate 3'-diphosphate (pppGpp) and guanosine 5'-diphosphate 3'-diphosphate (ppGpp) are specifically degraded by a manganese-dependent pyrophosphorylase present in spoT+ but not in spoT- strains of Escherichia coli, indicating that the enzyme is the spoT gene product. (PMID 365225 ) The kinetics of the GTP level during starvation suggests that GTP is a precursor of pppGpp. (PMID 793688 )
Structure
Synonyms
ValueSource
Guanosine 5'-triphosphate,3'-diphosphateChEBI
Guanosine pentaphosphateChEBI
Guanosine 5'-triphosphoric acid,3'-diphosphoric acidGenerator
Guanosine pentaphosphoric acidGenerator
Guanosine 3'-diphosphoric acid 5'-triphosphoric acidGenerator
3'-Diphosphate 5'-triphosphate, guanosineHMDB
Pentaphosphate, guanosineHMDB
Guanosine 3' diphosphate 5' triphosphateHMDB
5'-Triphosphate, guanosine 3'-diphosphateHMDB
Molecular FormulaC10H18N5O20P5
Average Mass683.1402
Monoisotopic Mass682.923320601
IUPAC Name{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Name{hydroxy[(2R,3S,4R,5R)-4-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-2-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid
CAS Registry Number38918-96-6
SMILES
[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O
InChI Identifier
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
InChI KeyKCPMACXZAITQAX-UUOKFMHZSA-N