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Record Information
Version	2.0
Creation Date	2012-05-31 14:39:19 -0600
Update Date	2015-06-03 17:19:47 -0600
Secondary Accession Numbers	ECMDB20324
Identification
Name:	ppGp
Description	Ppgp belongs to the class of Purine Ribonucleoside 3',5'-Bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. (inferred from compound structure)<br/><br/>Unusual guanosine nucleotides guanosine 5'-diphosphate 3'-diphosphate (ppGpp, also known as MSI) and guanosine 5'-diphosphate 3'-monophosphate (ppGp, also known as MSIII) accumulate to high concentrations in wild-type cells of Escherichia coli during amino acid starvation. (PMID 6117328)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa090538> Close
Synonyms:	Guanosine 5'-diphosphate-3'-monophosphate Guanosine 5'-diphosphoric acid-3'-monophosphoric acid GUANOSINE-3'-MONOPHOSPHATE-5'-DIPHOSPHATE GUANOSINE-3'-monophosphoric acid-5'-diphosphoric acid MsIII
Chemical Formula:	C10H16N5O14P3
Weight:	Average: 523.1804 Monoisotopic: 522.990659781
InChI Key:	HEYSFDAMRDTCJM-UUOKFMHZSA-N
InChI:	InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(28-30(18,19)20)3(27-9)1-26-32(24,25)29-31(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
CAS number:	58902-76-4
IUPAC Name:	{[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:	[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-3-yl]oxyphosphonic acid
SMILES:	[H][C@]1(COP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Purine ribonucleoside diphosphates
Alternative Parents	Purine ribonucleoside 3',5'-bisphosphates Pentose phosphates Ribonucleoside 3'-phosphates Glycosylamines 6-oxopurines Hypoxanthines Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Aminopyrimidines and derivatives Pyrimidones N-substituted imidazoles Vinylogous amides Heteroaromatic compounds Tetrahydrofurans Secondary alcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Primary amines
Substituents	Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Ribonucleoside 3'-phosphate Pentose-5-phosphate Pentose phosphate Glycosyl compound N-glycosyl compound 6-oxopurine Pentose monosaccharide Hypoxanthine Monosaccharide phosphate Organic pyrophosphate Imidazopyrimidine Purine Pyrimidone Aminopyrimidine Monoalkyl phosphate Pyrimidine Phosphoric acid ester Organic phosphoric acid derivative N-substituted imidazole Monosaccharide Alkyl phosphate Azole Imidazole Heteroaromatic compound Vinylogous amide Tetrahydrofuran Secondary alcohol Organoheterocyclic compound Azacycle Oxacycle Organic oxygen compound Amine Alcohol Hydrocarbon derivative Organic oxide Organopnictogen compound Organic nitrogen compound Organonitrogen compound Organooxygen compound Primary amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.23 g/L ALOGPS logP -1.1 ALOGPS logP -3.3 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 0.81 ChemAxon pKa (Strongest Basic) 4.89 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 15 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 295.8 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 107.82 m³·mol⁻¹ ChemAxon Polarizability 40.1 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_4_25) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0901230000-72a9b4dbaf4875976180 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0900100000-4e617da3770d77439b8e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-1900000000-d00fcb654b2e93eb0edb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0fk9-0900170000-3fb3bca8bf08b7192d24 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0fb9-5900000000-e4b68b3286ac5cf45b0e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9300000000-af81ec3c0ada17c3ad84 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 188347 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-1055 EcoCyc ID CPD0-1055 Ligand Expo G3D