Record Information
Version1.0
Created at2020-04-17 18:46:02 UTC
Updated at2020-11-18 16:38:55 UTC
CannabisDB IDCDB004877
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2'-Deoxyguanosine 5'-monophosphate
Description2'-Deoxyguanosine 5'-monophosphate, also known as deoxyguanylic acid or 2'-deoxy-GMP, belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. 2'-Deoxyguanosine 5'-monophosphate is a moderately basic compound (based on its pKa). 2'-Deoxyguanosine 5'-monophosphate exists in all living species, ranging from bacteria to humans. Within humans, 2'-deoxyguanosine 5'-monophosphate participates in a number of enzymatic reactions. In particular, 2'-deoxyguanosine 5'-monophosphate can be converted into dGDP; which is mediated by the enzyme guanylate kinase. In addition, 2'-deoxyguanosine 5'-monophosphate can be converted into deoxyguanosine through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In humans, 2'-deoxyguanosine 5'-monophosphate is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase. 2'-Deoxyguanosine 5'-monophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
2'-Deoxy-GMPChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphate)ChEBI
2'-Deoxyguanosine 5'-phosphateChEBI
2'-Deoxyguanylic acidChEBI
2'-dGMPChEBI
Deoxy-GMPChEBI
Deoxyguanosine 5'-monophosphateChEBI
Deoxyguanosine 5'-phosphateChEBI
Deoxyguanosine monophosphateChEBI
Deoxyguanylic acidChEBI
dGMPChEBI
2'-Deoxyguanosine 5'-(dihydrogen phosphoric acid)Generator
2'-Deoxyguanosine 5'-phosphoric acidGenerator
2'-DeoxyguanylateGenerator
Deoxyguanosine 5'-monophosphoric acidGenerator
Deoxyguanosine 5'-phosphoric acidGenerator
Deoxyguanosine monophosphoric acidGenerator
DeoxyguanylateGenerator
2'-Deoxyguanosine 5'-monophosphoric acidGenerator
2'-Deoxy-5'-GMPHMDB
2'-Deoxy-5'-guanylateHMDB
2'-Deoxy-5'-guanylic acidHMDB
2'-Deoxy-guanosine 5'-(dihydrogen phosphate)HMDB
2'-Deoxy-guanosine 5'-phosphateHMDB
2'-Deoxy-guanosine phosphateHMDB
2'-Deoxyguanosine-5'-phosphateHMDB
2'-DG-5'-MPHMDB
Deoxyguanosine-phosphateHMDB
Guanine ribosideHMDB
2'-Deoxyguanosine 5'-phosphate, ion (1+)HMDB
2'-Deoxyguanosine 5'-phosphate, disodium saltHMDB
Chemical FormulaC10H14N5O7P
Average Molecular Weight347.22
Monoisotopic Molecular Weight347.0631
IUPAC Name{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Namedeoxyguanylate
CAS Registry Number902-04-5
SMILES
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1
InChI Identifier
InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
InChI KeyLTFMZDNNPPEQNG-KVQBGUIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside monophosphate
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)2.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area181.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.55 m³·mol⁻¹ChemAxon
Polarizability29.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2'-Deoxyguanosine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9412000000-b0aa92c3ffa6b5b0890cSpectrum
Predicted GC-MS2'-Deoxyguanosine 5'-monophosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dm-9422100000-bc551a9549f9ae975b71Spectrum
Predicted GC-MS2'-Deoxyguanosine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0fr2-0598000000-21b063e2aff7146d8568Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-d2858e957ac8a4c91e79Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004j-9203000000-40bcf8d5e1ae6813c4f7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-dab30b9a6de3477fa70eSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-6109000000-6e5f13e1030d907bf450Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-c3273057674f4f74157bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-6009000000-303a1b69aa5c35e59b53Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-5a760c04146b7ec031d7Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-d435ed7c5cdb98529682Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-41c0a9342f54a46fa4e4Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-68f72700dfdbb0374a85Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000j-0905000000-26458e3261a5441d9304Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udr-1900000000-7a7e7e8e0b0145b7230dSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-a0ce6815866f122bcce0Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901000000-415ae3ba37bc56d4a402Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-bd375d50d1fb3f236468Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-6585941fd6af257d9a96Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-303e1f2bb06730d8520dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0901000000-e4234086a26601ce5af3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-566d720734de1bad5cd6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-5d4689698c352d2a2f45Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-6309000000-10f0b25fe6368edd1660Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-d531006102bbcb9090d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-a08be881b0ccce87df8aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Inosine triphosphate pyrophosphataseITPA20pQ9BY32 details
Deoxyguanosine kinase, mitochondrialDGUOK2p13Q16854 details
Guanylate kinaseGUK11q32-q41Q16774 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Inosine triphosphate pyrophosphataseITPA20pQ9BY32 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001044
DrugBank IDDB04457
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022388
KNApSAcK IDC00019356
Chemspider ID58570
KEGG Compound IDC00362
BioCyc IDDGMP
BiGG ID34744
Wikipedia LinkDeoxyguanosine_monophosphate
METLIN IDNot Available
PubChem Compound65059
PDB IDNot Available
ChEBI ID16192
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

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
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
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
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
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
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
General function:
Involved in ATP binding
Specific function:
Required for the phosphorylation of several deoxyribonucleosides and certain nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DGUOK
Uniprot ID:
Q16854
Molecular weight:
32055.53
General function:
Involved in guanylate kinase activity
Specific function:
Essential for recycling GMP and indirectly, cGMP.
Gene Name:
GUK1
Uniprot ID:
Q16774
Molecular weight:
21725.41
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2

Only showing the first 10 proteins. There are 18 proteins in total.