(1'r,2's)-9-(2-Hydroxy-3'-Keto-Cyclopenten-1-Yl)Adenine

Identification

Name
(1'r,2's)-9-(2-Hydroxy-3'-Keto-Cyclopenten-1-Yl)Adenine
Accession Number
DB03216  (EXPT00427)
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: 233.2266
Monoisotopic: 233.091274621
Chemical Formula
C10H11N5O2
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAdenosylhomocysteinaseNot AvailableHuman
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
5287610
PubChem Substance
46505345
ChemSpider
4449940
HET
ADC
PDB Entries
1a7a

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 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

Taxonomy

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
show 1 more
Substituents
1,3-substituted cyclopentyl purine nucleoside / 6-aminopurine / Imidazopyrimidine / Purine / Aminopyrimidine / Imidolactam / Pyrimidine / N-substituted imidazole / Azole / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Adenosylhomocysteinase
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:10