2'-deoxy-N-(naphthalen-1-ylmethyl)guanosine 5'-(dihydrogen phosphate)

Identification

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Name
2'-deoxy-N-(naphthalen-1-ylmethyl)guanosine 5'-(dihydrogen phosphate)
Accession Number
DB08237
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 487.4024
Monoisotopic: 487.125684595
Chemical Formula
C21H22N5O7P
InChI Key
COMPKRGNHXOXMN-GVDBMIGSSA-N
InChI
InChI=1S/C21H22N5O7P/c27-15-8-17(33-16(15)10-32-34(29,30)31)26-11-23-18-19(26)24-21(25-20(18)28)22-9-13-6-3-5-12-4-1-2-7-14(12)13/h1-7,11,15-17,27H,8-10H2,(H2,29,30,31)(H2,22,24,25,28)/t15-,16+,17+/m0/s1
IUPAC Name
{[(2R,3S,5R)-3-hydroxy-5-{2-[(naphthalen-1-ylmethyl)amino]-6-oxo-6,9-dihydro-1H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C=NC2=C1N=C(NCC1=CC=CC3=C1C=CC=C3)NC2=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDNA polymerase kappaNot AvailableHumans
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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
46937134
PubChem Substance
99444708
ChemSpider
25060415
HET
N2G
PDB Entries
2w8k / 2w8l

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 Solubility0.478 mg/mLALOGPS
logP0.31ALOGPS
logP0.98ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.12ChemAxon
pKa (Strongest Basic)1.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area167.53 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.82 m3·mol-1ChemAxon
Polarizability47.48 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9131
Blood Brain Barrier+0.7791
Caco-2 permeable-0.7133
P-glycoprotein substrateSubstrate0.6112
P-glycoprotein inhibitor INon-inhibitor0.7085
P-glycoprotein inhibitor IINon-inhibitor0.8723
Renal organic cation transporterNon-inhibitor0.874
CYP450 2C9 substrateNon-substrate0.8321
CYP450 2D6 substrateNon-substrate0.8192
CYP450 3A4 substrateSubstrate0.532
CYP450 1A2 substrateNon-inhibitor0.7929
CYP450 2C9 inhibitorNon-inhibitor0.7725
CYP450 2D6 inhibitorNon-inhibitor0.8626
CYP450 2C19 inhibitorNon-inhibitor0.8666
CYP450 3A4 inhibitorNon-inhibitor0.777
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8294
Ames testNon AMES toxic0.6624
CarcinogenicityNon-carcinogens0.7559
BiodegradationNot ready biodegradable0.9932
Rat acute toxicity2.5700 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8666
hERG inhibition (predictor II)Non-inhibitor0.6026
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 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

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
6-oxopurines / Hypoxanthines / Naphthalenes / Aminopyrimidines and derivatives / Monoalkyl phosphates / Secondary alkylarylamines / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Tetrahydrofurans
show 7 more
Substituents
Purine 2'-deoxyribonucleoside monophosphate / 6-oxopurine / Hypoxanthine / Naphthalene / Imidazopyrimidine / Purine / Aminopyrimidine / Pyrimidone / Secondary aliphatic/aromatic amine / Monoalkyl phosphate
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
DNA polymerase specifically involved in DNA repair. Plays an important role in translesion synthesis, where the normal high-fidelity DNA polymerases cannot proceed and DNA synthesis stalls. Dependi...
Gene Name
POLK
Uniprot ID
Q9UBT6
Uniprot Name
DNA polymerase kappa
Molecular Weight
98807.815 Da
References
  1. 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]

Drug created on September 15, 2010 15:30 / Updated on June 04, 2019 06:55