NAV

N-naphthalen-1-ylmethyl-2'-[3,5-dimethoxybenzamido]-2'-deoxy-adenosine

Identification

Generic Name
N-naphthalen-1-ylmethyl-2'-[3,5-dimethoxybenzamido]-2'-deoxy-adenosine
DrugBank Accession Number
DB03331
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 570.5958
Monoisotopic: 570.222682722
Chemical Formula
C30H30N6O6
Synonyms
  • 2'-Deoxy-2'-[(3,5-dimethoxybenzoyl)amino]-N-(1-naphthylmethyl)adenosine

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlyceraldehyde-3-phosphate dehydrogenase, testis-specificNot 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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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 2'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Purine 2'-deoxyribonucleosides
Direct Parent
Purine 2'-deoxyribonucleosides
Alternative Parents
6-alkylaminopurines / Glycosylamines / Dimethoxybenzenes / Naphthalenes / Benzamides / Anisoles / Benzoyl derivatives / Phenoxy compounds / Secondary alkylarylamines / Alkyl aryl ethers
show 14 more
Substituents
6-alkylaminopurine / 6-aminopurine / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminopyrimidine / Anisole / Aromatic heteropolycyclic compound / Azacycle
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
OARVXDFNTLYMCJ-JVUUKAHWSA-N
InChI
InChI=1S/C30H30N6O6/c1-40-20-10-19(11-21(12-20)41-2)29(39)35-24-26(38)23(14-37)42-30(24)36-16-34-25-27(32-15-33-28(25)36)31-13-18-8-5-7-17-6-3-4-9-22(17)18/h3-12,15-16,23-24,26,30,37-38H,13-14H2,1-2H3,(H,35,39)(H,31,32,33)/t23-,24-,26-,30-/m1/s1
IUPAC Name
N-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-(6-{[(naphthalen-1-yl)methyl]amino}-9H-purin-9-yl)oxolan-3-yl]-3,5-dimethoxybenzamide
SMILES
[H]N(CC1=CC=CC2=CC=CC=C12)C1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3N([H])C(=O)C3=CC(OC)=CC(OC)=C3)C2=NC=N1

References

General References
Not Available
PubChem Compound
446186
PubChem Substance
46506163
ChemSpider
393610
BindingDB
50100471
ChEMBL
CHEMBL303934
ZINC
ZINC000026189382
PDBe Ligand
NMD
PDB Entries
1i32

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0182 mg/mLALOGPS
logP2.62ALOGPS
logP2.18Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.3Chemaxon
pKa (Strongest Basic)3.72Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area152.88 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity154.45 m3·mol-1Chemaxon
Polarizability60.07 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8656
Blood Brain Barrier-0.5773
Caco-2 permeable-0.7844
P-glycoprotein substrateSubstrate0.6503
P-glycoprotein inhibitor INon-inhibitor0.8675
P-glycoprotein inhibitor IINon-inhibitor0.646
Renal organic cation transporterNon-inhibitor0.8942
CYP450 2C9 substrateNon-substrate0.7974
CYP450 2D6 substrateNon-substrate0.8446
CYP450 3A4 substrateSubstrate0.618
CYP450 1A2 substrateNon-inhibitor0.8644
CYP450 2C9 inhibitorNon-inhibitor0.8399
CYP450 2D6 inhibitorNon-inhibitor0.8927
CYP450 2C19 inhibitorNon-inhibitor0.9021
CYP450 3A4 inhibitorNon-inhibitor0.8275
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7371
Ames testNon AMES toxic0.8896
CarcinogenicityNon-carcinogens0.8946
BiodegradationNot ready biodegradable0.9948
Rat acute toxicity2.6011 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9792
hERG inhibition (predictor II)Inhibitor0.5243
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

Targets

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Details1. Glyceraldehyde-3-phosphate dehydrogenase, testis-specific
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
May play an important role in regulating the switch between different pathways for energy production during spermiogenesis and in the spermatozoon. Required for sperm motility and male fertility (B...
Gene Name
GAPDHS
Uniprot ID
O14556
Uniprot Name
Glyceraldehyde-3-phosphate dehydrogenase, testis-specific
Molecular Weight
44500.835 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. [Article]
  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. [Article]
  3. 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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52