Identification
- Generic Name
- Guanosine-5'-Monophosphate
- DrugBank Accession Number
- DB01972
- Background
Guanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Guanosine-5'-Monophosphate (DB01972)
- Weight
- Average: 363.2206
Monoisotopic: 363.057998961 - Chemical Formula
- C10H14N5O8P
- Synonyms
- Not Available
- External IDs
- E 626
- E-626
- INS NO.626
- INS-626
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGuanylate kinase Not Available Humans UResponse regulator PleD Not Available Caulobacter crescentus (strain ATCC 19089 / CB15) UDNA polymerase Not Available Enterobacteria phage RB69 UDisks large homolog 4 Not Available Humans UGMP reductase 1 Not Available Humans UcGMP-specific 3',5'-cyclic phosphodiesterase Not Available Humans UHistidine triad nucleotide-binding protein 1 Not Available Humans UBifunctional purine biosynthesis protein PURH Not Available Humans UAmidophosphoribosyltransferase Not Available Bacillus subtilis (strain 168) UProtein-glutamine gamma-glutamyltransferase E Not Available Humans UBifunctional protein PyrR Not Available Bacillus caldolyticus UXanthine phosphoribosyltransferase Not Available Escherichia coli (strain K12) UAmidophosphoribosyltransferase Not Available Escherichia coli (strain K12) UBifunctional adenosylcobalamin biosynthesis protein CobU Not Available Salmonella 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / 6-oxopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound show 31 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- guanosine 5'-phosphate, purine ribonucleoside 5'-monophosphate (CHEBI:17345) / Ribonucleotides (C00144)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 16597955EP
- CAS number
- 85-32-5
- 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[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001397
- KEGG Compound
- C00144
- PubChem Compound
- 6804
- PubChem Substance
- 46504973
- ChemSpider
- 6545
- BindingDB
- 50010318
- ChEBI
- 17345
- ChEMBL
- CHEMBL283807
- ZINC
- ZINC000002159505
- PDBe Ligand
- G
- PDB Entries
- 1a97 / 1ao0 / 1c9k / 1ecb / 1ex7 / 1g7c / 1g9t / 1gky / 1hgx / 1hmp … show 149 more
Clinical Trials
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
Property Value Source Water Solubility 3.56 mg/mL ALOGPS logP -2 ALOGPS logP -3.1 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 1.3 Chemaxon pKa (Strongest Basic) 0.43 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 201.75 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 75.49 m3·mol-1 Chemaxon Polarizability 30.7 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5068 Blood Brain Barrier + 0.9216 Caco-2 permeable - 0.7598 P-glycoprotein substrate Non-substrate 0.6314 P-glycoprotein inhibitor I Non-inhibitor 0.9289 P-glycoprotein inhibitor II Non-inhibitor 0.9846 Renal organic cation transporter Non-inhibitor 0.9489 CYP450 2C9 substrate Non-substrate 0.8647 CYP450 2D6 substrate Non-substrate 0.835 CYP450 3A4 substrate Non-substrate 0.5544 CYP450 1A2 substrate Non-inhibitor 0.8702 CYP450 2C9 inhibitor Non-inhibitor 0.9285 CYP450 2D6 inhibitor Non-inhibitor 0.914 CYP450 2C19 inhibitor Non-inhibitor 0.9266 CYP450 3A4 inhibitor Non-inhibitor 0.9525 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9855 Ames test Non AMES toxic 0.8998 Carcinogenicity Non-carcinogens 0.9046 Biodegradation Not ready biodegradable 0.9672 Rat acute toxicity 2.2703 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9744 hERG inhibition (predictor II) Non-inhibitor 0.8654
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 189.2289759 predictedDarkChem Lite v0.1.0 [M-H]- 192.4771759 predictedDarkChem Lite v0.1.0 [M-H]- 193.0746759 predictedDarkChem Lite v0.1.0 [M-H]- 169.5583 predictedDeepCCS 1.0 (2019) [M+H]+ 190.1320759 predictedDarkChem Lite v0.1.0 [M+H]+ 193.3471759 predictedDarkChem Lite v0.1.0 [M+H]+ 193.5766759 predictedDarkChem Lite v0.1.0 [M+H]+ 171.95387 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.1810759 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.0999759 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.5046759 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.90862 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- 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
- 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
- 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
- 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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52