2-({8-[(3R)-3-AMINOPIPERIDIN-1-YL]-1,3-DIMETHYL-2,6-DIOXO-1,2,3,6-TETRAHYDRO-7H-PURIN-7-YL}METHYL)BENZONITRILE

Identification

Name
2-({8-[(3R)-3-AMINOPIPERIDIN-1-YL]-1,3-DIMETHYL-2,6-DIOXO-1,2,3,6-TETRAHYDRO-7H-PURIN-7-YL}METHYL)BENZONITRILE
Accession Number
DB08743
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: 393.4423
Monoisotopic: 393.191323015
Chemical Formula
C20H23N7O2
InChI Key
XJNKUWDMCBZMTG-OAHLLOKOSA-N
InChI
InChI=1S/C20H23N7O2/c1-24-17-16(18(28)25(2)20(24)29)27(11-14-7-4-3-6-13(14)10-21)19(23-17)26-9-5-8-15(22)12-26/h3-4,6-7,15H,5,8-9,11-12,22H2,1-2H3/t15-/m1/s1
IUPAC Name
2-({8-[(3R)-3-aminopiperidin-1-yl]-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl}methyl)benzonitrile
SMILES
[H][C@@]1(N)CCCN(C1)C1=NC2=C(N1CC1=CC=CC=C1C#N)C(=O)N(C)C(=O)N2C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
6914643
PubChem Substance
99445214
ChemSpider
5290523
ZINC
ZINC000003839213
PDBe Ligand
XIH
PDB Entries
2gbi / 3g0d

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 Solubility0.861 mg/mLALOGPS
logP1.03ALOGPS
logP1.5ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)9.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.49 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.23 m3·mol-1ChemAxon
Polarizability41.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.94
Caco-2 permeable-0.5906
P-glycoprotein substrateSubstrate0.6977
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.8372
Renal organic cation transporterNon-inhibitor0.5898
CYP450 2C9 substrateNon-substrate0.8266
CYP450 2D6 substrateNon-substrate0.7407
CYP450 3A4 substrateSubstrate0.6694
CYP450 1A2 substrateNon-inhibitor0.8291
CYP450 2C9 inhibitorNon-inhibitor0.8039
CYP450 2D6 inhibitorNon-inhibitor0.9578
CYP450 2C19 inhibitorNon-inhibitor0.8444
CYP450 3A4 inhibitorNon-inhibitor0.7088
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9038
Ames testNon AMES toxic0.5219
CarcinogenicityNon-carcinogens0.8969
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.5210 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.511
hERG inhibition (predictor II)Inhibitor0.843
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 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 xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Benzonitriles / Dialkylarylamines / Pyrimidones / Aminopiperidines / Aminoimidazoles / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds
show 9 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Benzonitrile / Dialkylarylamine / 3-aminopiperidine / Pyrimidone / Aminoimidazole / Monocyclic benzene moiety
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, aminopiperidine (CHEBI:46581)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 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]

Drug created on September 15, 2010 15:34 / Updated on June 12, 2020 10:52

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