THEOPHYLLINE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC R03DA04
UNII 0I55128JYK
EPA CompTox DTXSID5021336

Structure

InChI Key ZFXYFBGIUFBOJW-UHFFFAOYSA-N
Smiles Cn1c(=O)c2[nH]cnc2n(C)c1=O
InChI
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)

Physicochemical Descriptors

Property Name Value
Molecular Formula C7H8N4O2
Molecular Weight 180.17
AlogP -1.04
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 72.68
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 13.0

Bioactivity

Mechanism of Action Action Reference
Adenosine receptor antagonist ANTAGONIST PubMed PubMed PubMed PubMed Wikipedia
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Organism : Homo sapiens
P27815 ENSG00000065989
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Organism : Homo sapiens
Q07343 ENSG00000184588
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4C
Organism : Homo sapiens
Q08493 ENSG00000105650
Protein: Phosphodiesterase 4
Description: cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Organism : Homo sapiens
Q08499 ENSG00000113448
Protein: Phosphodiesterase 3
Description: cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B
Organism : Homo sapiens
Q13370 ENSG00000152270
Protein: Phosphodiesterase 3
Description: cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
Organism : Homo sapiens
Q14432 ENSG00000172572
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1A
- 92000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1B
- 92000 - - 46
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1C
- - - - 13
Enzyme Phosphodiesterase Phosphodiesterase 2 Phosphodiesterase 2A
- - - - 0
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3A
- - - - 30
Enzyme Phosphodiesterase Phosphodiesterase 3 Phosphodiesterase 3B
- 90000 - 77000 30
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- 50000-81000 - 56800-56800 26-39
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
- - - - 13
Enzyme Transferase
- 75000 - - -
Enzyme
- 50000-81000 - 56800-56800 26-39
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 7-7
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
28200 19000-28000 12000 700-26000 2100
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 1-90
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Unclassified protein
- - - 86400 -
Assay Description Organism Bioactivity Reference
Inhibition of [3H]-CHA binding to rat brain membrane Adenosine A1 receptor Rattus norvegicus 700.0 nM
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 23.1 %
Inhibition of Adenylate Cyclase in Rat adipocytes None 940.0 nM
Bronchodilatory activity in vitro by tracheal tone inhibition at 30 ug/mL in guinea pig tracheal muscle. Cavia porcellus 60.0 %
Inhibition of PDE4 at 200 uM None 39.0 %
Inhibition of rolipram binding to PDE4 at 100 uM None 27.0 %
Inhibition of phosphodiesterase 5A at 100 uM Sus scrofa 13.0 %
Concentration required to inhibit 50% activity of phosphodiesterase IB isoenzyme at 100 uM. None 46.0 %
Inhibition of phosphodiesterase Ic isoenzyme Bos taurus 13.0 %
Concentration required to inhibit 50% activity of phosphodiesterase II isoenzyme at 100 uM None 0.0 %
Concentration required to inhibit 50% activity of phosphodiesterase III isoenzyme at 100 uM Bos taurus 30.0 %
Inhibition of phosphodiesterase 4 at 100 uM Bos taurus 26.0 %
Percent inhibition of PCA reaction in anesthetized rats after 11.7 mg/kg intraduodenal administration for 15 min Rattus norvegicus 42.4 %
Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 15 min Rattus norvegicus 51.9 %
Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 24 hr r Rattus norvegicus 0.0 %
Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 3 hr Rattus norvegicus 52.5 %
Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 6 hr Rattus norvegicus 13.0 %
Percent inhibition of PCA reaction in anesthetized rats at 11.7 mg/kg peroral administration for 3 hr Rattus norvegicus 25.1 %
Antiallergic activity evaluated as percent inhibition at peroral dose of 100 mg/kg in rats Rattus norvegicus 66.0 %
Percent inhibition of serum creatinine by the compound given as ratio of Cr value in treated to vehicle treated ones after intraperitoneal administration of 10 mg/kg of compound to rats(vehicle 182.5+/-3.4) Rattus norvegicus 2.0 %
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 182.5+/-3.4) Rattus norvegicus 5.0 %
Antagonist binding of 2-chloro-[3H]-adenosine to rat brain Rattus norvegicus 150.0 nM
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 6.9 %
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 100 uM Cavia porcellus 7.0 %
Dissociation constant of the compound None 400.0 nM
Binding affinity for adenosine A2a receptor by using as [3H]ZM-241385 radioligand in membranes from HEK-A2A cells Homo sapiens 0.6 nM
Binding affinity for adenosine A1 receptor by using as [3H]CPX iradioligand n membranes from Chinese hamster ovary cells Homo sapiens 0.6 nM
Binding affinity for adenosine A3 receptor by displacement of specific binding of [125I]AB-MECA in membranes from CHO-A3 cells Homo sapiens 14.0 nM
Inhibition of COX2 at 100 uM by scintillation proximity assay None 30.0 %
Inhibition of PDE4 at 200 uM None 39.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -4.4 %
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 0.8 %
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 2.5 %
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 -25.5 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 90.11 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 72.46 %
Inhibition of Mongrel dog ventricular muscle cAMP phosphodiesterase using adenosine 3',5' monophosphate as substrate at 100 uM by scintillation counting analysis in presence of [8-14C]adenosine relative to control Canis lupus familiaris 51.0 %
Antiallergic activity in antiovalbumin serum sensitized guinea pig lung slices assessed as inhibition of ovalbumin-induced histamine release at 1.5 mM preincubated for 5 mins followed by ovalbumin challenge measured after 15 mins by fluorometric analysis relative to control Cavia porcellus 50.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -24.23 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 7.82 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 1.07 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 16.98 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 9.61 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.65 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 7.56 %
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 -0.3 %
Inhibition of Streptococcus pyogenes SrtA deltaN81 mutant expressed in Escherichia coli BL21(DE3) at 100 uM using Abz-LPETA-Dap(Dnp) as substrate preincubated for 10 mins followed by substrate addition measured every min for 2.5 hrs by fluorimetric assay relative to control Streptococcus pyogenes 2.3 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 37.24 %
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 0.2 % 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 0.2 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Hungary
Romania
Slovakia
Vietnam

Cross References

Resources Reference
ChEBI 28177
ChEMBL CHEMBL190
DrugBank DB00277
DrugCentral 2620
FDA SRS 0I55128JYK
Human Metabolome Database HMDB0001889
Guide to Pharmacology 413
KEGG C07130
PDB TEP
PharmGKB PA451647
PubChem 91268
SureChEMBL SCHEMBL4915
ZINC ZINC000018043251
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