Identification

Generic Name
5-monophosphate-9-beta-D-ribofuranosyl xanthine
DrugBank Accession Number
DB02309
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 365.214
Monoisotopic: 365.049291465
Chemical Formula
C10H14N4O9P
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBifunctional purine biosynthesis protein PURHNot AvailableHumans
UHypoxanthine-guanine phosphoribosyltransferaseNot 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
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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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XHDARDSMKMUDDI-UUOKFMHZSA-O
InChI
InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H4,12,13,17,18,19,20,21)/p+1/t3-,5-,6-,9-/m1/s1
IUPAC Name
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-9lambda5-purin-9-ylium
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CNC2=C1NC(=O)NC2=O

References

General References
Not Available
PubChem Compound
6323540
PubChem Substance
46504859
ChemSpider
4883470
PDBe Ligand
XMP
PDB Entries
1lol / 1m9n / 1mei / 1mew / 1p4r / 1pkx / 1pl0 / 1qk5 / 2cu0 / 2czf
show 12 more

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 Solubility2.1 mg/mLALOGPS
logP-0.61ALOGPS
logP-6.2ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area194.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.38 m3·mol-1ChemAxon
Polarizability30.66 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9761
Blood Brain Barrier+0.8245
Caco-2 permeable-0.7539
P-glycoprotein substrateNon-substrate0.641
P-glycoprotein inhibitor INon-inhibitor0.9362
P-glycoprotein inhibitor IINon-inhibitor0.9664
Renal organic cation transporterNon-inhibitor0.961
CYP450 2C9 substrateNon-substrate0.7283
CYP450 2D6 substrateNon-substrate0.8372
CYP450 3A4 substrateNon-substrate0.5456
CYP450 1A2 substrateNon-inhibitor0.8405
CYP450 2C9 inhibitorNon-inhibitor0.9368
CYP450 2D6 inhibitorNon-inhibitor0.8923
CYP450 2C19 inhibitorNon-inhibitor0.9179
CYP450 3A4 inhibitorNon-inhibitor0.9767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9744
Ames testNon AMES toxic0.9075
CarcinogenicityNon-carcinogens0.906
BiodegradationReady biodegradable0.5344
Rat acute toxicity2.2549 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.944
hERG inhibition (predictor II)Non-inhibitor0.768
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.Promotes insulin receptor/INSR autophosphorylation and is involved in INSR internalization (PubMed:25687571).
Gene Name
ATIC
Uniprot ID
P31939
Uniprot Name
Bifunctional purine biosynthesis protein PURH
Molecular Weight
64615.255 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]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role...
Gene Name
HPRT1
Uniprot ID
P00492
Uniprot Name
Hypoxanthine-guanine phosphoribosyltransferase
Molecular Weight
24579.155 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]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14