(1'R,2'S)-9-(2-Hydroxy-3'-Keto-Cyclopenten-1-yl)Adenine

Identification

Generic Name
(1'R,2'S)-9-(2-Hydroxy-3'-Keto-Cyclopenten-1-yl)Adenine
DrugBank Accession Number
DB03216
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 233.2266
Monoisotopic: 233.091274621
Chemical Formula
C10H11N5O2
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
UAdenosylhomocysteinaseNot 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 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Nucleoside and nucleotide analogues
Sub Class
Cyclopentyl nucleosides
Direct Parent
1,3-substituted cyclopentyl purine nucleosides
Alternative Parents
6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Azacyclic compounds / Primary amines / Organopnictogen compounds
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Substituents
1,2-diol / 1,3-substituted cyclopentyl purine nucleoside / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
RQPALADHFYHEHK-CHKWXVPMSA-N
InChI
InChI=1S/C10H11N5O2/c11-9-7-10(13-3-12-9)15(4-14-7)5-1-2-6(16)8(5)17/h1-6,8,16-17H,(H2,11,12,13)/t5-,6+,8+/m1/s1
IUPAC Name
(1S,2S,5R)-5-(6-amino-9H-purin-9-yl)cyclopent-3-ene-1,2-diol
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1C=C[C@H](O)[C@H]1O

References

General References
Not Available
PubChem Compound
5287610
PubChem Substance
46505345
ChemSpider
4449940
PDBe Ligand
ADC
PDB Entries
1a7a

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 Solubility6.86 mg/mLALOGPS
logP-0.63ALOGPS
logP-1.2ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)13.19ChemAxon
pKa (Strongest Basic)5.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.08 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.44 m3·mol-1ChemAxon
Polarizability22.39 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.9207
Caco-2 permeable-0.513
P-glycoprotein substrateNon-substrate0.6781
P-glycoprotein inhibitor INon-inhibitor0.9326
P-glycoprotein inhibitor IINon-inhibitor0.7593
Renal organic cation transporterNon-inhibitor0.9226
CYP450 2C9 substrateNon-substrate0.8444
CYP450 2D6 substrateNon-substrate0.8247
CYP450 3A4 substrateNon-substrate0.6799
CYP450 1A2 substrateNon-inhibitor0.8058
CYP450 2C9 inhibitorNon-inhibitor0.8368
CYP450 2D6 inhibitorNon-inhibitor0.8086
CYP450 2C19 inhibitorNon-inhibitor0.6535
CYP450 3A4 inhibitorNon-inhibitor0.9158
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7592
Ames testAMES toxic0.7172
CarcinogenicityNon-carcinogens0.9193
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.5712 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9502
hERG inhibition (predictor II)Non-inhibitor0.8383
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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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Details
1. Adenosylhomocysteinase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nad binding
Specific Function
Adenosylhomocysteine is a competitive inhibitor of S-adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylation...
Gene Name
AHCY
Uniprot ID
P23526
Uniprot Name
Adenosylhomocysteinase
Molecular Weight
47715.715 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]

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