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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL113
CHEMBL113
Compound Name CAFFEINE
ChEMBL Synonyms THEINE | CAFCIT | Caffeine | COFFEINE | Cafcit | CAFFEINE CITRATE | METHYLTHEOBROMINE | CAFFEINE, CITRATED
Max Phase 4 (Approved)
Trade Names CAFFEINE CITRATE | CAFCIT
Molecular Formula C8H10N4O2

Additional synonyms for CHEMBL113 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN1C(=O)N(C)c2ncn(C)c2C1=O
Standard InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4 ...
Download InChI
Standard InChI Key RYYVLZVUVIJVGH-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL113

Molecule Features

CHEMBL113 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:N Availability Type:Over-The-Counter

Mechanism of Action

Mechanism of Action ChEMBL Target References
Adenosine receptor antagonist Adenosine receptor FDA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
PAIND010146EFO:0003843PAIN1ClinicalTrials
ATRIAL FIBRILLATIOND001281EFO:0000275ATRIAL FIBRILLATION3ClinicalTrials
LIVER DISEASESD008107EFO:0001421LIVER DISEASE1ClinicalTrials
DYSPNEAD004417HP:0002094DYSPNEA2ClinicalTrials
MIGRAINE DISORDERSD008881EFO:0003821MIGRAINE DISORDER3ClinicalTrials
PREMATURE BIRTHD047928EFO:0003917PREMATURE BIRTH3ClinicalTrials
CORONARY ARTERY DISEASED003324EFO:0000378CORONARY ARTERY DISEASE3ClinicalTrials
RETINOPATHY OF PREMATURITYD012178EFO:1001158RETINOPATHY OF PREMATURITY2ClinicalTrials
AMBLYOPIAD000550HP:0000646AMBLYOPIA1ClinicalTrials
COCAINE-RELATED DISORDERSD019970EFO:0002610COCAINE DEPENDENCE2ClinicalTrials
ATTENTION DEFICIT DISORDER WITH HYPERACTIVITYD001289EFO:0003888ATTENTION DEFICIT HYPERACTIVITY DISORDER4ATC
PARKINSON DISEASED010300EFO:0002508PARKINSON'S DISEASE3ClinicalTrials

Clinical Data

ClinicalTrials.gov CAFFEINE
The Cochrane Collaboration CAFFEINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL113. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL5185 Glutamate racemase Helicobacter pylori J99 0.999
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.997
CHEMBL6007 Transient receptor potential cation channel subfamily A member 1 Homo sapiens 0.995
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.989
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.977
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.970
CHEMBL4975 Adenosine A1 receptor Bos taurus 0.904
CHEMBL255 Adenosine A2b receptor Homo sapiens 0.889
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.799
CHEMBL2039 Monoamine oxidase B Homo sapiens 0.642
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.612
CHEMBL4360 Monocarboxylate transporter 1 Homo sapiens 0.592
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.403
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.400
CHEMBL273 Serotonin 1a (5-HT1a) receptor Rattus norvegicus 0.315
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.279
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 0.265



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2605 Adenosine A2a receptor Cavia porcellus 1.000
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 1.000
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 1.000
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 1.000
CHEMBL255 Adenosine A2b receptor Homo sapiens 1.000
CHEMBL6007 Transient receptor potential cation channel subfamily A member 1 Homo sapiens 0.996
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.996
CHEMBL5185 Glutamate racemase Helicobacter pylori J99 0.996
CHEMBL2592 Adenosine A2b receptor Rattus norvegicus 0.994
CHEMBL2039 Monoamine oxidase B Homo sapiens 0.967
CHEMBL1951 Monoamine oxidase A Homo sapiens 0.891
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.711
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.667
CHEMBL4975 Adenosine A1 receptor Bos taurus 0.494
CHEMBL3155 Serotonin 7 (5-HT7) receptor Homo sapiens 0.467
CHEMBL273 Serotonin 1a (5-HT1a) receptor Rattus norvegicus 0.419
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.398
CHEMBL4360 Monocarboxylate transporter 1 Homo sapiens 0.371
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.334

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
194.2 194.0804 -0.1 0 58.44 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 0 0 6 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- .52 -.63 -.63 1 14 0.58

Structural Alerts

There are no structural alerts for CHEMBL113

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06B - PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS
N06BC - Xanthine derivatives
N06BC01 - caffeine

ChemSpider ChemSpider:RYYVLZVUVIJVGH-UHFFFAOYSA-N
DailyMed caffeine caffeine citrate
PubChem SID: 104171124 SID: 11110908 SID: 124879556 SID: 144208883 SID: 144210330 SID: 17389997 SID: 26732615 SID: 26752751 SID: 49718178 SID: 50105397 SID: 50105398 SID: 90341215
Wikipedia Caffeine Caffeine_(data_page)

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL113



ACToR 58-08-2
Atlas caffeine
BindingDB 10849
Brenda 51266 7965 882
ChEBI 27732
DrugBank DB00201
DrugCentral 463
eMolecules 493944 27517656
EPA CompTox Dashboard DTXSID0020232
FDA SRS 3G6A5W338E
Guide to Pharmacology 407
Human Metabolome Database HMDB0001847
IBM Patent System F5DC77C5C625DA4D47FA47B7105235AE
KEGG Ligand C07481
LINCS LSM-2026
Mcule MCULE-3362813910
Metabolights MTBLC27732
Nikkaji J2.330B
NMRShiftDB 10016316
PDBe CFF
PharmGKB PA448710
PubChem 2519
PubChem: Thomson Pharma 14772978
Rhea 27732
SureChEMBL SCHEMBL5671
ZINC ZINC000000001084

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/RYYVLZVUVIJVGH-UHFFFAOYSA-N spacer
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