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

Identification

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Name
(2R,3R,4S,5R)-2-[6-amino-8-[(3,4-dichlorophenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Accession Number
DB07045
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: 441.269
Monoisotopic: 440.076658508
Chemical Formula
C17H18Cl2N6O4
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

Pharmacology

Indication
Not Available
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
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
25195347
PubChem Substance
99443516
ChemSpider
23337032
BindingDB
32373
ChEMBL
CHEMBL516357
HET
3BK
PDB Entries
3fzk

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 Solubility0.511 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

Taxonomy

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
show 11 more
Substituents
Purine nucleoside / N-glycosyl compound / Glycosyl compound / 6-aminopurine / Pentose monosaccharide / Imidazopyrimidine / Purine / Benzylamine / 1,2-dichlorobenzene / Secondary aliphatic/aromatic amine
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:10592235]
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. [PubMed:10592235]

Drug created on September 15, 2010 15:18 / Updated on June 04, 2019 06:33