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Identification
Name(1'r,2's)-9-(2-Hydroxy-3'-Keto-Cyclopenten-1-Yl)Adenine
Accession NumberDB03216  (EXPT00427)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 233.2266
Monoisotopic: 233.091274621
Chemical FormulaC10H11N5O2
InChI KeyInChIKey=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[[email protected]](O)[[email protected]]1O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassCyclopentyl nucleosides
Direct Parent1,3-substituted cyclopentyl purine nucleosides
Alternative Parents
Substituents
  • 1,3-substituted cyclopentyl purine nucleoside
  • 1,2-substituted cyclopentyl purine nucleoside
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Cyclic alcohol
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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 methylations via regulation of the intracellular concentration of adenosylhomocysteine.
Gene Name:
AHCY
Uniprot ID:
P23526
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23