Guanosine-5'-Monophosphate

Identification

Name
Guanosine-5'-Monophosphate
Accession Number
DB01972  (EXPT00246)
Type
Small Molecule
Groups
Experimental
Description

Guanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
E 626 / E-626 / INS NO.626 / INS-626
Categories
Not Available
UNII
16597955EP
CAS number
85-32-5
Weight
Average: 363.2206
Monoisotopic: 363.057998961
Chemical Formula
C10H14N5O8P
InChI Key
RQFCJASXJCIDSX-UUOKFMHZSA-N
InChI
InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
NC1=NC2=C(N=CN2[[email protected]@H]2O[[email protected]](COP(O)(O)=O)[[email protected]@H](O)[[email protected]]2O)C(=O)N1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGuanylate kinaseNot AvailableHuman
UResponse regulator PleDNot AvailableCaulobacter crescentus (strain ATCC 19089 / CB15)
UDNA polymeraseNot AvailableEnterobacteria phage RB69
UDisks large homolog 4Not AvailableHuman
UGMP reductase 1Not AvailableHuman
UcGMP-specific 3',5'-cyclic phosphodiesteraseNot AvailableHuman
UHistidine triad nucleotide-binding protein 1Not AvailableHuman
UBifunctional purine biosynthesis protein PURHNot AvailableHuman
UAmidophosphoribosyltransferaseNot AvailableBacillus subtilis (strain 168)
UProtein-glutamine gamma-glutamyltransferase ENot AvailableHuman
UBifunctional protein PyrRNot AvailableBacillus caldolyticus
UXanthine phosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
UAmidophosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
UBifunctional adenosylcobalamin biosynthesis protein CobUNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Purine MetabolismMetabolic
Glutamate MetabolismMetabolic
Adenosine Deaminase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
HomocarnosinosisDisease
Tobramycin Action PathwayDrug action
Arbekacin Action PathwayDrug action
Methacycline Action PathwayDrug action
2-Hydroxyglutric Aciduria (D And L Form)Disease
AICA-RibosiduriaDisease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDisease
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Hyperinsulinism-Hyperammonemia SyndromeDisease
Mercaptopurine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria type IDisease
Azithromycin Action PathwayDrug action
Telithromycin Action PathwayDrug action
Streptomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Lesch-Nyhan Syndrome (LNS)Disease
Myoadenylate deaminase deficiencyDisease
Lincomycin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
Clindamycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01397
KEGG Compound
C00144
PubChem Compound
6804
PubChem Substance
46504973
ChemSpider
6545
BindingDB
50010318
ChEBI
17345
ChEMBL
CHEMBL283807
HET
G
PDB Entries
1a97 / 1ao0 / 1c9k / 1ecb / 1ex7 / 1g7c / 1g9t / 1gky / 1hgx / 1hmp
show 106 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.56 mg/mLALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.05ChemAxon
pKa (Strongest Basic)1.73ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.75 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.49 m3·mol-1ChemAxon
Polarizability30.7 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5068
Blood Brain Barrier+0.9216
Caco-2 permeable-0.7598
P-glycoprotein substrateNon-substrate0.6314
P-glycoprotein inhibitor INon-inhibitor0.9289
P-glycoprotein inhibitor IINon-inhibitor0.9846
Renal organic cation transporterNon-inhibitor0.9489
CYP450 2C9 substrateNon-substrate0.8647
CYP450 2D6 substrateNon-substrate0.835
CYP450 3A4 substrateNon-substrate0.5544
CYP450 1A2 substrateNon-inhibitor0.8702
CYP450 2C9 inhibitorNon-inhibitor0.9285
CYP450 2D6 inhibitorNon-inhibitor0.914
CYP450 2C19 inhibitorNon-inhibitor0.9266
CYP450 3A4 inhibitorNon-inhibitor0.9525
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9855
Ames testNon AMES toxic0.8998
CarcinogenicityNon-carcinogens0.9046
BiodegradationNot ready biodegradable0.9672
Rat acute toxicity2.2703 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9744
hERG inhibition (predictor II)Non-inhibitor0.8654
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (6 TMS)GC-MSsplash10-014i-1942000000-27fc2e135f86071ba4d7
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1942000000-27fc2e135f86071ba4d7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0941000000-245c5258141d8d2a9fa5
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0udi-0901000000-fbce35f7dfa73ab5fc11
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0udi-0900000000-764722cc1b8cc2aaa480
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0udi-0900000000-c268cdce8dfd6c39fa3c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-03di-0409000000-309e438ad8b6162df850
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0udi-0904000000-cf72d0459316801b014e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-0900000000-abc7bfe7620db1c34775
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-01t9-9114000000-9a1071a2e17ea3ca268c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-01t9-9113000000-05a8989070e3b89138f1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-01t9-9114000000-9a1071a2e17ea3ca268c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-01t9-9113000000-05a8989070e3b89138f1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0409000000-309e438ad8b6162df850
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0904000000-cf72d0459316801b014e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-abc7bfe7620db1c34775
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Pyrimidones / Monoalkyl phosphates / N-substituted imidazoles / Vinylogous amides
show 10 more
Substituents
Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Pentose monosaccharide / Imidazopyrimidine
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
guanosine 5'-phosphate, purine ribonucleoside 5'-monophosphate (CHEBI:17345) / Ribonucleotides (C00144)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Guanylate kinase activity
Specific Function
Essential for recycling GMP and indirectly, cGMP.
Gene Name
GUK1
Uniprot ID
Q16774
Uniprot Name
Guanylate kinase
Molecular Weight
21725.41 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Caulobacter crescentus (strain ATCC 19089 / CB15)
Pharmacological action
Unknown
General Function
Signal transducer activity
Specific Function
Response regulator that is part of a signal transduction pathway controlling cell differentiation in the swarmer-to-stalked cell transition.Catalyzes the condensation of two GTP molecules to the cy...
Gene Name
pleD
Uniprot ID
Q9A5I5
Uniprot Name
Response regulator PleD
Molecular Weight
49623.365 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Enterobacteria phage RB69
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Replicates the viral genomic DNA. This polymerase possesses two enzymatic activities: DNA synthesis (polymerase) and an exonucleolytic activity that degrades single-stranded DNA in the 3'- to 5'-di...
Gene Name
43
Uniprot ID
Q38087
Uniprot Name
DNA polymerase
Molecular Weight
104612.37 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Scaffold protein binding
Specific Function
Interacts with the cytoplasmic tail of NMDA receptor subunits and shaker-type potassium channels. Required for synaptic plasticity associated with NMDA receptor signaling. Overexpression or depleti...
Gene Name
DLG4
Uniprot ID
P78352
Uniprot Name
Disks large homolog 4
Molecular Weight
80494.615 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining t...
Gene Name
GMPR
Uniprot ID
P36959
Uniprot Name
GMP reductase 1
Molecular Weight
37418.58 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase c binding
Specific Function
Hydrolyzes purine nucleotide phosphoramidates with a single phosphate group, including adenosine 5'monophosphoramidate (AMP-NH2), adenosine 5'monophosphomorpholidate (AMP-morpholidate) and guanosin...
Gene Name
HINT1
Uniprot ID
P49773
Uniprot Name
Histidine triad nucleotide-binding protein 1
Molecular Weight
13801.815 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.Promotes insulin receptor/INSR autophosphorylation and is involved in INSR internalization (PubMed:25687571).
Gene Name
ATIC
Uniprot ID
P31939
Uniprot Name
Bifunctional purine biosynthesis protein PURH
Molecular Weight
64615.255 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Catalyzes the formation of phosphoribosylamine from phosphoribosylpyrophosphate (PRPP) and glutamine.
Gene Name
purF
Uniprot ID
P00497
Uniprot Name
Amidophosphoribosyltransferase
Molecular Weight
51691.455 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity, transferring acyl groups
Specific Function
Catalyzes the calcium-dependent formation of isopeptide cross-links between glutamine and lysine residues in various proteins, as well as the conjugation of polyamines to proteins. Involved in the ...
Gene Name
TGM3
Uniprot ID
Q08188
Uniprot Name
Protein-glutamine gamma-glutamyltransferase E
Molecular Weight
76631.26 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Bacillus caldolyticus
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Regulates transcriptional attenuation of the pyrimidine nucleotide (pyr) operon by binding in a uridine-dependent manner to specific sites on pyr mRNA. This disrupts an antiterminator hairpin in th...
Gene Name
pyrR
Uniprot ID
P41007
Uniprot Name
Bifunctional protein PyrR
Molecular Weight
19937.85 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Xanthine phosphoribosyltransferase activity
Specific Function
Acts on guanine, xanthine and to a lesser extent hypoxanthine.
Gene Name
gpt
Uniprot ID
P0A9M5
Uniprot Name
Xanthine phosphoribosyltransferase
Molecular Weight
16970.455 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Transferase activity, transferring glycosyl groups
Specific Function
Catalyzes the formation of phosphoribosylamine from phosphoribosylpyrophosphate (PRPP) and glutamine. Can also use NH(3) in place of glutamine.
Gene Name
purF
Uniprot ID
P0AG16
Uniprot Name
Amidophosphoribosyltransferase
Molecular Weight
56487.49 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Gtp binding
Specific Function
Catalyzes ATP-dependent phosphorylation of adenosylcobinamide and addition of GMP to adenosylcobinamide phosphate.
Gene Name
cobU
Uniprot ID
Q05599
Uniprot Name
Bifunctional adenosylcobalamin biosynthesis protein CobU
Molecular Weight
19901.7 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:07