(2R,3R,4S,5R)-2-[6-amino-8-[(3,4-dichlorophenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Identification

Generic Name
(2R,3R,4S,5R)-2-[6-amino-8-[(3,4-dichlorophenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
DrugBank Accession Number
DB07045
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 441.269
Monoisotopic: 440.076658508
Chemical Formula
C17H18Cl2N6O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBAG family molecular chaperone regulator 1Not AvailableHumans
UHeat shock cognate 71 kDa proteinNot 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
Adverseeffects
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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 nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / Benzylamines / Dichlorobenzenes / Secondary alkylarylamines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Aminoimidazoles
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Substituents
1,2-dichlorobenzene / 6-aminopurine / Alcohol / Amine / Aminoimidazole / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle
show 34 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
VBJKVZXRYLCYGQ-XNIJJKJLSA-N
InChI
InChI=1S/C17H18Cl2N6O4/c18-8-2-1-7(3-9(8)19)4-21-17-24-11-14(20)22-6-23-15(11)25(17)16-13(28)12(27)10(5-26)29-16/h1-3,6,10,12-13,16,26-28H,4-5H2,(H,21,24)(H2,20,22,23)/t10-,12-,13-,16-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-(6-amino-8-{[(3,4-dichlorophenyl)methyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
SMILES
[H][C@]1(CO)O[C@@]([H])(N2C(NCC3=CC=C(Cl)C(Cl)=C3)=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
25195347
PubChem Substance
99443516
ChemSpider
23337032
BindingDB
32373
ChEMBL
CHEMBL516357
ZINC
ZINC000040913495
PDBe Ligand
3BK
PDB Entries
3fzk

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 Solubility0.511 mg/mLALOGPS
logP1.39ALOGPS
logP1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area151.57 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.08 m3·mol-1ChemAxon
Polarizability42.57 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9809
Blood Brain Barrier+0.8443
Caco-2 permeable-0.7083
P-glycoprotein substrateNon-substrate0.506
P-glycoprotein inhibitor INon-inhibitor0.9391
P-glycoprotein inhibitor IINon-inhibitor0.8885
Renal organic cation transporterNon-inhibitor0.8563
CYP450 2C9 substrateNon-substrate0.8754
CYP450 2D6 substrateNon-substrate0.8237
CYP450 3A4 substrateNon-substrate0.5104
CYP450 1A2 substrateNon-inhibitor0.7736
CYP450 2C9 inhibitorNon-inhibitor0.8731
CYP450 2D6 inhibitorNon-inhibitor0.8757
CYP450 2C19 inhibitorNon-inhibitor0.903
CYP450 3A4 inhibitorNon-inhibitor0.6481
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9112
Ames testNon AMES toxic0.7784
CarcinogenicityNon-carcinogens0.8441
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5737 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9534
hERG inhibition (predictor II)Non-inhibitor0.565
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

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor signaling protein activity
Specific Function
Inhibits the chaperone activity of HSP70/HSC70 by promoting substrate release. Inhibits the pro-apoptotic function of PPP1R15A, and has anti-apoptotic activity. Markedly increases the anti-cell dea...
Gene Name
BAG1
Uniprot ID
Q99933
Uniprot Name
BAG family molecular chaperone regulator 1
Molecular Weight
38778.46 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Unfolded protein binding
Specific Function
Acts as a repressor of transcriptional activation. Inhibits the transcriptional coactivator activity of CITED1 on Smad-mediated transcription. Chaperone. Component of the PRP19-CDC5L complex that f...
Gene Name
HSPA8
Uniprot ID
P11142
Uniprot Name
Heat shock cognate 71 kDa protein
Molecular Weight
70897.565 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. [Article]

Drug created on September 15, 2010 21:18 / Updated on June 12, 2020 16:52