Showing Compound Card for Guanosine monophosphate (CDB004911)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (64)transporters (1) Show 144 proteinsXML
Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version1.0
Created at2020-04-17 18:49:39 UTC
Updated at2020-12-07 19:11:15 UTC
CannabisDB IDCDB004911
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGuanosine monophosphate
DescriptionGuanosine monophosphate, also known as guanylic acid or 5'-GMP, 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. Guanosine monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Guanosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, guanosine monophosphate participates in a number of enzymatic reactions. In particular, guanosine triphosphate and guanosine monophosphate can be biosynthesized from diguanosine tetraphosphate; which is catalyzed by the enzyme bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]. In addition, guanosine monophosphate can be biosynthesized from guanosine diphosphate; which is mediated by the enzyme ectonucleoside triphosphate diphosphohydrolase 5. In humans, guanosine monophosphate is involved in purine metabolism. A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase. Outside of the human body, Guanosine monophosphate has been detected, but not quantified in, several different foods, such as rosemaries, common chokecherries, pigeon pea, rices, and horseradish tree. This could make guanosine monophosphate a potential biomarker for the consumption of these foods. Guanosine monophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC10H14N5O8P
Average Molecular Weight363.22
Monoisotopic Molecular Weight363.058
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
Traditional Nameguanylate
CAS Registry Number85-32-5
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
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
InChI KeyRQFCJASXJCIDSX-UUOKFMHZSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility369 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-3.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)0.38ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.49 m³·mol⁻¹ChemAxon
Polarizability30.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGuanosine monophosphate, 6 TMS, GC-MS Spectrumsplash10-014i-1942000000-27fc2e135f86071ba4d7Spectrum
GC-MSGuanosine monophosphate, non-derivatized, GC-MS Spectrumsplash10-014i-1942000000-27fc2e135f86071ba4d7Spectrum
GC-MSGuanosine monophosphate, non-derivatized, GC-MS Spectrumsplash10-014i-0941000000-245c5258141d8d2a9fa5Spectrum
Predicted GC-MSGuanosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9722000000-9155df338c7516c297b6Spectrum
Predicted GC-MSGuanosine monophosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9522200000-3e2591b21841c753ec13Spectrum
Predicted GC-MSGuanosine monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Cyclic nucleotide-gated cation channel alpha-3CNGA32q11.2Q16281 details
Metal Bindings
Receptors
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8APDE8A15q25.3O60658 details
cGMP-dependent 3',5'-cyclic phosphodiesterasePDE2A11q13.4O00408 details
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8BPDE8B5q13.3O95263 details
Concentrations Data
Not Available
HMDB IDHMDB0001397
DrugBank IDDB01972
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030896
KNApSAcK IDC00019635
Chemspider ID6545
KEGG Compound IDC00144
BioCyc IDGMP
BiGG ID34024
Wikipedia LinkGuanosine_monophosphate
METLIN ID6216
PubChem Compound6804
PDB IDNot Available
ChEBI ID17345
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 144 proteins in total.

Show All

Enzymes

Enzyme Details
1. 5'-nucleotidase
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Enzyme Details
2. Cytosolic 5'-nucleotidase 1B
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Enzyme Details
3. Cytosolic 5'-nucleotidase 1A
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Enzyme Details
4. 5'(3')-deoxyribonucleotidase, cytosolic type
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Enzyme Details
5. 5'(3')-deoxyribonucleotidase, mitochondrial
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Enzyme Details
6. Ectonucleoside triphosphate diphosphohydrolase 1
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Enzyme Details
7. Soluble calcium-activated nucleotidase 1
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
Enzyme Details
8. Ectonucleoside triphosphate diphosphohydrolase 3
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
Enzyme Details
9. Inosine triphosphate pyrophosphatase
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Enzyme Details
10. Adenine phosphoribosyltransferase
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535

Transporters

Enzyme Details
1. Cyclic nucleotide-gated cation channel alpha-3
General function:
Involved in ion channel activity
Specific function:
Visual signal transduction is mediated by a G-protein coupled cascade using cGMP as second messenger. This protein can be activated by cyclic GMP which leads to an opening of the cation channel and thereby causing a depolarization of cone photoreceptors. Induced a flickering channel gating, weakened the outward rectification in the presence of extracellular calcium, increased sensitivity for L-cis diltiazem and enhanced the cAMP efficacy of the channel when coexpressed with CNGB3. Essential for the generation of light-evoked electrical responses in the red-, green- and blue sensitive cones
Gene Name:
CNGA3
Uniprot ID:
Q16281
Molecular weight:
78837.4

Only showing the first 10 proteins. There are 144 proteins in total.

Show All