You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name2',5'-DIDEOXY-ADENOSINE 3'-MONOPHOSPHATE
Accession NumberDB06843
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: 315.2224
Monoisotopic: 315.073255095
Chemical FormulaC10H14N5O5P
InChI KeyNFGZMOICZSFFLB-DSYKOEDSSA-N
InChI
InChI=1S/C10H14N5O5P/c1-5-6(20-21(16,17)18)2-7(19-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7H,2H2,1H3,(H2,11,12,13)(H2,16,17,18)/t5-,6+,7-/m1/s1
IUPAC Name
{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-methyloxolan-3-yl]oxy}phosphonic acid
SMILES
[H][C@]1(C)O[C@]([H])(C[C@]1([H])OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Guanine nucleotide-binding protein G(s) subunit alpha isoforms shortProteinunknownNot AvailableHumanP63092 details
Adenylate cyclase type 2ProteinunknownNot AvailableHumanQ08462 details
Adenylate cyclase type 5ProteinunknownNot AvailableHumanO95622 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6576
Blood Brain Barrier+0.8974
Caco-2 permeable-0.6292
P-glycoprotein substrateNon-substrate0.5683
P-glycoprotein inhibitor INon-inhibitor0.8328
P-glycoprotein inhibitor IINon-inhibitor0.9657
Renal organic cation transporterNon-inhibitor0.9164
CYP450 2C9 substrateNon-substrate0.772
CYP450 2D6 substrateNon-substrate0.8292
CYP450 3A4 substrateSubstrate0.5311
CYP450 1A2 substrateNon-inhibitor0.8264
CYP450 2C9 inhibitorNon-inhibitor0.8531
CYP450 2D6 inhibitorNon-inhibitor0.8953
CYP450 2C19 inhibitorNon-inhibitor0.8186
CYP450 3A4 inhibitorNon-inhibitor0.92
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9038
Ames testNon AMES toxic0.659
CarcinogenicityNon-carcinogens0.8549
BiodegradationNot ready biodegradable0.984
Rat acute toxicity2.4805 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.8924
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 Solubility2.35 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area145.61 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.01 m3·mol-1ChemAxon
Polarizability28.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Signal transducer activity
Specific Function:
Guanine nucleotide-binding proteins (G proteins) function as transducers in numerous signaling pathways controlled by G protein-coupled receptors (GPCRs) (PubMed:17110384). Signaling involves the activation of adenylyl cyclases, resulting in increased levels of the signaling molecule cAMP (PubMed:26206488, PubMed:8702665). GNAS functions downstream of several GPCRs, including beta-adrenergic re...
Gene Name:
GNAS
Uniprot ID:
P63092
Molecular Weight:
45664.205 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
Human
Pharmacological action
unknown
General Function:
Protein heterodimerization activity
Specific Function:
Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:15385642). Down-stream signaling cascades mediate changes in gene expression patterns and lead to increased IL6 production. Functions in signaling cascades downstream of the muscarinic acetylcholine receptors (By similarity).
Gene Name:
ADCY2
Uniprot ID:
Q08462
Molecular Weight:
123602.25 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
Human
Pharmacological action
unknown
General Function:
Protein heterodimerization activity
Specific Function:
Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:15385642, PubMed:26206488, PubMed:24700542). Mediates signaling downstream of ADRB1 (PubMed:24700542). Regulates the increase of free cytosolic Ca(2+) in response to increased blood glucose levels and contributes to the regulation of Ca(2+)-dependent insulin secretion (PubMed:24740569).
Gene Name:
ADCY5
Uniprot ID:
O95622
Molecular Weight:
138906.37 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 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:17 / Updated on August 17, 2016 12:24