Identification
NameNebularine
Accession NumberDB04440  (EXPT02701)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
N-D-Ribosylpurine
Purine nucleoside
Purine riboside
External IDs Not Available
Product Ingredients 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
Categories
UNIIB8B604PS4P
CAS number550-33-4
WeightAverage: 252.2267
Monoisotopic: 252.085854892
Chemical FormulaC10H12N4O4
InChI KeyMRWXACSTFXYYMV-FDDDBJFASA-N
InChI
InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1
IUPAC Name
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
SMILES
[H][[email protected]]1(CO)O[[email protected]@]([H])(N2C=NC3=CN=CN=C23)[[email protected]]([H])(O)[[email protected]]1([H])O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Adenosine deaminaseProteinunknownNot AvailableHumanP00813 details
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Purine Riboside.Approved
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Purine Riboside.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Purine Riboside.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Purine Riboside.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Purine Riboside.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Purine Riboside.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Purine Riboside.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Purine Riboside.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Purine Riboside.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Purine Riboside.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Purine Riboside.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Purine Riboside.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Purine Riboside.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Purine Riboside.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)181 °CPhysProp
water solubility1E+005 mg/LMERCK (1989)
Predicted Properties
PropertyValueSource
Water Solubility16.8 mg/mLALOGPS
logP-0.99ALOGPS
logP-1.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.18 m3·mol-1ChemAxon
Polarizability23.51 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5193
Blood Brain Barrier+0.8419
Caco-2 permeable-0.87
P-glycoprotein substrateNon-substrate0.7028
P-glycoprotein inhibitor INon-inhibitor0.9767
P-glycoprotein inhibitor IINon-inhibitor0.9111
Renal organic cation transporterNon-inhibitor0.9415
CYP450 2C9 substrateNon-substrate0.812
CYP450 2D6 substrateNon-substrate0.8277
CYP450 3A4 substrateNon-substrate0.5748
CYP450 1A2 substrateNon-inhibitor0.8872
CYP450 2C9 inhibitorNon-inhibitor0.9628
CYP450 2D6 inhibitorNon-inhibitor0.967
CYP450 2C19 inhibitorNon-inhibitor0.9469
CYP450 3A4 inhibitorNon-inhibitor0.9882
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9683
Ames testNon AMES toxic0.876
CarcinogenicityNon-carcinogens0.93
BiodegradationNot ready biodegradable0.5979
Rat acute toxicity2.1732 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9802
hERG inhibition (predictor II)Non-inhibitor0.8942
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0gba-0960000000-02588b36be524da1fbdbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-0690000000-3132e9cf975c9d333807View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-30611d46c742b20458a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-bf687a37f1a8fdee4b9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-1ca445719eb772d826e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-d4186191baed33ece266View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-fe942a1442dc2ba58705View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0940000000-558c13580fe37e7be7ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-c0a60904cd95924d259fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-8900000000-dece14475c7e39a2463eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0790000000-52cdec17cf806f6a8d60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-825da67e9ee8ead415d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9800000000-eeb587fff62d67752a0cView in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleosides
Direct ParentPurine nucleosides
Alternative ParentsGlycosylamines / Pentoses / Purines and purine derivatives / Pyrimidines and pyrimidine derivatives / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds
SubstituentsPurine nucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Imidazopyrimidine / Purine / Monosaccharide / N-substituted imidazole / Pyrimidine / Heteroaromatic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorspurine ribonucleoside (CHEBI:18255 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Uniprot Name:
Adenosine deaminase
Molecular Weight:
40764.13 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 ]
  3. 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 June 13, 2005 07:24 / Updated on September 01, 2017 11:17