2'-Deoxyguanosine-5'-Monophosphate

Identification

Name
2'-Deoxyguanosine-5'-Monophosphate
Accession Number
DB04457  (EXPT01182)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
7EAM4TG712
CAS number
902-04-5
Weight
Average: 347.2212
Monoisotopic: 347.063084339
Chemical Formula
C10H14N5O7P
InChI Key
LTFMZDNNPPEQNG-KVQBGUIXSA-N
InChI
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
IUPAC Name
{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDeoxynucleotide monophosphate kinaseNot AvailableEnterobacteria phage T4
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
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
Thioguanine Action PathwayDrug action
Purine MetabolismMetabolic
AICA-RibosiduriaDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Azathioprine Action PathwayDrug action
Adenosine Deaminase DeficiencyDisease
Molybdenum Cofactor DeficiencyDisease
Xanthinuria Type IDisease
Xanthinuria Type IIDisease
Purine MetabolismMetabolic
Purine Nucleoside Phosphorylase DeficiencyDisease
Mercaptopurine Action PathwayDrug action
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Adenylosuccinate Lyase DeficiencyDisease
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001044
KEGG Compound
C00362
PubChem Compound
65059
PubChem Substance
46507156
ChemSpider
58570
ChEBI
16192
ChEMBL
CHEMBL477487
HET
DGP
PDB Entries
1dek / 1del / 1q9x / 1rnd / 1tlc / 1z4p / 2dwn / 2fc0 / 2jao / 2lrr
show 3 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 Solubility2.67 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)2.62ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area181.52 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.55 m3·mol-1ChemAxon
Polarizability29.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8342
Blood Brain Barrier+0.8619
Caco-2 permeable-0.751
P-glycoprotein substrateNon-substrate0.5222
P-glycoprotein inhibitor INon-inhibitor0.876
P-glycoprotein inhibitor IINon-inhibitor0.9604
Renal organic cation transporterNon-inhibitor0.9236
CYP450 2C9 substrateNon-substrate0.8691
CYP450 2D6 substrateNon-substrate0.8301
CYP450 3A4 substrateSubstrate0.5091
CYP450 1A2 substrateNon-inhibitor0.8519
CYP450 2C9 inhibitorNon-inhibitor0.9131
CYP450 2D6 inhibitorNon-inhibitor0.9136
CYP450 2C19 inhibitorNon-inhibitor0.9185
CYP450 3A4 inhibitorNon-inhibitor0.9258
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9713
Ames testNon AMES toxic0.7515
CarcinogenicityNon-carcinogens0.8428
BiodegradationNot ready biodegradable0.9826
Rat acute toxicity2.3758 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9536
hERG inhibition (predictor II)Non-inhibitor0.87
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0fr2-0598000000-21b063e2aff7146d8568
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-0900000000-d2858e957ac8a4c91e79
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-004j-9203000000-40bcf8d5e1ae6813c4f7
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/MSsplash10-004j-9203000000-40bcf8d5e1ae6813c4f7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-dab30b9a6de3477fa70e
1H NMR Spectrum1D NMRNot Applicable
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 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine deoxyribonucleotides
Direct Parent
Purine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Purines and purine derivatives / Monoalkyl phosphates / Hydroxypyrimidines / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds
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Substituents
Purine 2'-deoxyribonucleoside monophosphate / Imidazopyrimidine / Purine / Hydroxypyrimidine / Monoalkyl phosphate / N-substituted imidazole / Organic phosphoric acid derivative / Phosphoric acid ester / Alkyl phosphate / Pyrimidine
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
deoxyguanosine phosphate, purine 2'-deoxyribonucleoside 5'-monophosphate, guanyl deoxyribonucleotide (CHEBI:16192) / Deoxyribonucleotides (C00362)

Targets

Kind
Protein
Organism
Enterobacteria phage T4
Pharmacological action
Unknown
General Function
Atp binding
Specific Function
Phosphorylates dGMP, dTMP and 5-hydroxymethyl-dCMP while excluding dCMP and dAMP. The phosphorylation of 5-hydroxymethyl-dCMP represents the first step in the replacement of cytosine by hydroxymeth...
Gene Name
1
Uniprot ID
P04531
Uniprot Name
Deoxynucleotide monophosphate kinase
Molecular Weight
27328.9 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
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name
thyA
Uniprot ID
P0A884
Uniprot Name
Thymidylate synthase
Molecular Weight
30479.475 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]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:50