NAV

2'-Deoxy-2'-[(3,5-dimethoxybenzoyl)amino]-N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]adenosine

Identification

Generic Name
2'-Deoxy-2'-[(3,5-dimethoxybenzoyl)amino]-N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]adenosine
DrugBank Accession Number
DB04477
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 560.601
Monoisotopic: 560.238332786
Chemical Formula
C29H32N6O6
Synonyms
  • N-1,2,3,4-Tetrahydronaphth-1-yl-2'-[3,5-dimethoxybenzamido]-2'-deoxy-adenosine
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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 / Tetralins / Dimethoxybenzenes / Benzamides / Phenoxy compounds / Anisoles / Benzoyl derivatives / Alkyl aryl ethers / Aminopyrimidines and derivatives
show 12 more
Substituents
6-alkylaminopurine / 6-aminopurine / Alcohol / Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteropolycyclic compound / Azacycle / Azole
show 36 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
FDZQGEIYGFPMOB-ZUURFMEUSA-N
InChI
InChI=1S/C29H32N6O6/c1-39-18-10-17(11-19(12-18)40-2)28(38)34-23-25(37)22(13-36)41-29(23)35-15-32-24-26(30-14-31-27(24)35)33-21-9-5-7-16-6-3-4-8-20(16)21/h3-4,6,8,10-12,14-15,21-23,25,29,36-37H,5,7,9,13H2,1-2H3,(H,34,38)(H,30,31,33)/t21-,22-,23-,25-,29-/m1/s1
IUPAC Name
N-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-(6-{[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-9H-purin-9-yl)oxolan-3-yl]-3,5-dimethoxybenzamide
SMILES
[H]N([C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N=CN=C12)N([H])[C@@H]1CCCC2=CC=CC=C12)C(=O)C1=CC(OC)=CC(OC)=C1

References

General References
Not Available
PubChem Compound
5289484
PubChem Substance
46506101
ChemSpider
4451444
ZINC
ZINC000058638411
PDBe Ligand
TND
PDB Entries
1i33

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 Solubility0.0444 mg/mLALOGPS
logP2.42ALOGPS
logP2.17Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.3Chemaxon
pKa (Strongest Basic)3.69Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area152.88 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity150.18 m3·mol-1Chemaxon
Polarizability59.53 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8977
Blood Brain Barrier-0.8826
Caco-2 permeable-0.7015
P-glycoprotein substrateSubstrate0.6548
P-glycoprotein inhibitor INon-inhibitor0.8206
P-glycoprotein inhibitor IINon-inhibitor0.6481
Renal organic cation transporterNon-inhibitor0.8702
CYP450 2C9 substrateNon-substrate0.7611
CYP450 2D6 substrateNon-substrate0.8326
CYP450 3A4 substrateSubstrate0.6745
CYP450 1A2 substrateNon-inhibitor0.7808
CYP450 2C9 inhibitorNon-inhibitor0.7766
CYP450 2D6 inhibitorNon-inhibitor0.8708
CYP450 2C19 inhibitorNon-inhibitor0.8621
CYP450 3A4 inhibitorNon-inhibitor0.6127
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7278
Ames testNon AMES toxic0.8278
CarcinogenicityNon-carcinogens0.9015
BiodegradationNot ready biodegradable0.9812
Rat acute toxicity2.1738 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.97
hERG inhibition (predictor II)Inhibitor0.5383
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/MSsplash10-03xr-0050090000-e4b667d778c242d01e63
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0cgi-0107390000-e0a0dc7ebba6b3026f27
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-0152190000-fa724f55d3926aba14e1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-5192870000-bb6ee4fc35a6513114fd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-0261490000-912a4bc52b641ad54422
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-0960720000-843c30243e047eae2d00
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-234.83427
predicted
DeepCCS 1.0 (2019)
[M+H]+236.72969
predicted
DeepCCS 1.0 (2019)
[M+Na]+243.82271
predicted
DeepCCS 1.0 (2019)

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