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148892-91-5 molecular structure
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trisodium hydrogen {[({[(2R,3S,4R,5R)-5-(2-amino-6-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]amino}phosphonate

ChemBase ID: 155143
Molecular Formular: C10H14N6Na3O13P3
Molecular Mass: 588.141153
Monoisotopic Mass: 587.95247727
SMILES and InChIs

SMILES:
c1nc2c(n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(NP(=O)(O)[O-])[O-])O)O)nc(nc2O)N.[Na+].[Na+].[Na+]
Canonical SMILES:
O[C@@H]1[C@@H](COP(=O)(OP(=O)(NP(=O)(O)[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1nc(N)nc2O.[Na+].[Na+].[Na+]
InChI:
InChI=1S/C10H17N6O13P3.3Na/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22;;;/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24);;;/q;3*+1/p-3/t3-,5-,6-,9-;;;/m1.../s1
InChIKey:
QGJNRMUNXAROIT-CYCLDIHTSA-K

Cite this record

CBID:155143 http://www.chembase.cn/molecule-155143.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
trisodium hydrogen {[({[(2R,3S,4R,5R)-5-(2-amino-6-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]amino}phosphonate
IUPAC Traditional name
trisodium hydrogen ({[(2R,3S,4R,5R)-5-(2-amino-6-hydroxypurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)aminophosphonate
Synonyms
β:γ-Imidoguanosine 5′-triphosphate trisodium salt hydrate
5′-Guanylyl-imidodiphosphate trisodium salt hydrate
GMP-PNP
Gpp(NH)p
Guanosine 5′-[β,γ-imido]triphosphate trisodium salt hydrate
CAS Number
148892-91-5
MDL Number
MFCD00084770
PubChem SID
162249281
24895020
PubChem CID
16219382

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
G0635 external link Add to cart Please log in.
Data Source Data ID
PubChem 16219382 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 0.23122565  H Acceptors 15 
H Donor LogD (pH = 5.5) -9.807186 
LogD (pH = 7.4) -10.796439  Log P -4.2329125 
Molar Refractivity 96.3259 cm3 Polarizability 39.54993 Å3
Polar Surface Area 310.65 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL expand Show data source
Apperance
white powder expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥85% (HPLC) expand Show data source
Shipped in
dry ice expand Show data source
Empirical Formula (Hill Notation)
C10H14N6Na3O13P3 · xH2O expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - G0635 external link
Application
Non-hydrolyzable analog of GTP; the preferred GTP analog to activate ADP-ribosylation factor.
Guanosine 5′-[β,γ-imido]triphosphate (GMP-PNP, Gpp(NH)p) is a non-hydrolyzable analog of GTP that binds and irreversibly activates G proteins. Gpp(NH)p is used in a variety of applications that involve GTP binding, including GTP-activation, GTP-inhibition, GTP transport, GTP hydrolysis, and GTP structure stabilization. Since a cycle of GTP binding, hydrolysis, and release is required for the initiation of protein translocation across the endoplasmic reticulum, guanosine 5′-[β,γ-imido]triphosphate is often used in studies of protein synthesis. Gpp(NH)p is used to activate ADP-ribosylation factors and to modulate G proteins involved in cell signaling, protein synthesis and other metabolic processes.
Biochem/physiol Actions
Binds and irreversibly activates G proteins.1 Since a cycle of GTP binding, hydrolysis, and release is required for the initiation of protein translocation across the endoplasmic reticulum, this non-hydrolyzable GTP analog is often used in studies of protein synthesis.2,3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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