CAFFEINE

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Synonyms
Status
Molecule Category Free-form
ATC D11AX26 N06BC01
UNII 3G6A5W338E
EPA CompTox DTXSID0020232

Structure

InChI Key RYYVLZVUVIJVGH-UHFFFAOYSA-N
Smiles Cn1c(=O)c2c(ncn2C)n(C)c1=O
InChI
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H10N4O2
Molecular Weight 194.19
AlogP -1.03
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 0.0
Polar Surface Area 61.82
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 14.0

Bioactivity

Mechanism of Action Action Reference
Adenosine receptor antagonist ANTAGONIST FDA PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 7250 - 10200 -
Enzyme Oxidoreductase
- - - - 16
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1A
- 70000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1B
- 70000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1C
- 70000 - - -
Enzyme Transferase
- 75000 - - -
Enzyme
- 74900-100000 - 10200 16
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 10
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- 63000 25119 17000-59000 30
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -2-104
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Assay Description Organism Bioactivity Reference
Tested for the binding affinity, for displacement of [125I]AB-MECA in membranes of CHO cells stably transfected with the rat A3-cDNA at the 10e-4 concentration (M) None 30.1 %
Percent inhibition of serum creatinine by the compound given as ratio of Cr value in treated to vehicle treated ones after intraperitoneal administration of 10 mg/kg of compound to rats(vehicle 4.41+/-0.16) Rattus norvegicus 35.0 %
Percent inhibition of serum creatinine by the compound given as ratio of Cr value in treated to vehicle treated ones after intraperitoneal administration of 1 mg/kg of compound to rats(vehicle 4.70+/-0.17) Rattus norvegicus 22.0 %
Percent inhibition of Urea nitrogen by the compound given as ratio of UN value in treated to vehicle treated ones after intraperitoneal administration of 10 mg/kg of compound to rats(vehicle 145.1+/-7.4) Rattus norvegicus 25.0 %
Percent inhibition of Urea nitrogen by the compound given as ratio of UN value in treated to vehicle treated ones after intraperitoneal administration of 1 mg/kg of compound to rats(vehicle 154.2+/-5) Rattus norvegicus 18.0 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 9.7 %
Antioxidant activity in rat liver microsomes assessed as inhibition of ethoxyresorufin O-deethylase activity at 1000 uM Rattus norvegicus 80.0 %
Displacement of [3H]MSX-2 from A2A receptor in rat brain striatal membrane at 100 uM by liquid scintillation counting Rattus norvegicus 58.0 %
Inhibition of COX2 at 100 uM by scintillation proximity assay None 30.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -1.4 %
Inhibition of [3H]NECA binding to human recombinant adenosine A3 receptor expressed in HEK293T cells at 100 uM by scintillation counting Homo sapiens 9.0 %
TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical)(Digoxin: 5 uM, Caffeine: 100 uM) in Caco-2 cells None 36.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens -1.8 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 22.1 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 3.2 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 103.59 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 90.35 %
Anticataleptic activity in rat assessed as inhibition at 3 mg/kg, po after 1 hr Rattus norvegicus 35.0 %
Anticataleptic activity in rat assessed as inhibition at 3 mg/kg, po after 4 hrs Rattus norvegicus 14.0 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 33.57 %
Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI insect cells at 50 uM preincubated for 30 mins followed by addition of p-tyramine as substrate measured over 45 mins by Amplex Red MAO assay relative to control Homo sapiens 33.0 %
Inhibition of recombinant human MAO-B expressed in baculovirus infected BTI insect cells at 50 uM preincubated for 30 mins followed by addition of p-tyramine as substrate measured over 45 mins by Amplex Red MAO assay relative to control Homo sapiens 16.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.733 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.1 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.1 %

Related Entries

Cross References

Resources Reference
ChEBI 27732
ChEMBL CHEMBL113
DrugBank DB00201
DrugCentral 463
FDA SRS 3G6A5W338E
Human Metabolome Database HMDB0001847
Guide to Pharmacology 407
KEGG C07481
PDB CFF
PharmGKB PA448710
PubChem 2519
SureChEMBL SCHEMBL5671
ZINC ZINC000000001084
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