CAFFEINE

Search structure
Synonyms:
Status: Approved (1948)
Entry Type: Small molecule
Molecule Category: Parent
ATC: D11AX26
UNII: 3G6A5W338E

Structure
InChI Key RYYVLZVUVIJVGH-UHFFFAOYSA-N
Smile 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

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Adenosine receptor antagonist
Primary Target
A1 receptor
A2A receptor
A2B receptor
A3 receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
45800-46000 18600-100000 85000 10000-10200
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family Atypical protein kinase FRAP subfamily
- 400000 - - -
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family
- 10000000 - - -
Enzyme Oxidoreductase
- - - 3600000-3800000 16
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1A
- 70000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1B
- 70000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 1 Phosphodiesterase 1C
- 70000 - - -
Enzyme Protease Metallo protease Metallo protease MG clan Metallo protease M24B subfamily
- - - - 17.5-38.75
Enzyme Transferase
- 74900-648000 - - 7.733
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -38.76--5.61
Epigenetic regulator Eraser Histone deacetylase HDAC class III
- - 690 - -
Ion channel Voltage-gated ion channel Transient receptor potential channel
61800 988000 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 660000 - - 9.7
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- 110000-117000 5510-25118.86 17000-59000 30.1
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group E Nuclear hormone receptor subfamily 2 group E member 1
- 7943.28 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -1.8-103.59
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- - - - 36
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 14000000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Attention Deficit Disorder with Hyperactivity 4 D001289 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Headache 3 D006261 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Toothache 3 D014098 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Hypoxia 3 D000860 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Obesity 3 D009765 ClinicalTrials
Common Cold 3 D003139 ClinicalTrials
Intermittent Claudication 3 D007383 ClinicalTrials
Neck Pain 3 D019547 ClinicalTrials
Dysmenorrhea 3 D004412 ClinicalTrials
Bronchopulmonary Dysplasia 3 D001997 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Parkinson Disease 3 D010300 ClinicalTrials
Migraine with Aura 3 D020325 ClinicalTrials
Back Pain 3 D001416 ClinicalTrials
Migraine without Aura 3 D020326 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Dyspnea 2 D004417 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Tension-Type Headache 2 D018781 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Sexual Dysfunction, Physiological 1 D012735 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Severe Acute Respiratory Syndrome 1 D045169 ClinicalTrials
Dermatitis, Atopic 1 D003876 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Psoriasis 1 D011565 ClinicalTrials
Arthritis, Rheumatoid 1 D001172 ClinicalTrials
Hepatitis C, Chronic 1 D019698 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Hypotension, Orthostatic 1 D007024 ClinicalTrials
Communicable Diseases 1 D003141 ClinicalTrials
Non-alcoholic Fatty Liver Disease 1 D065626 ClinicalTrials
Spinal Cord Injuries 1 D013119 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Voice Disorders 1 D014832 ClinicalTrials
Chronic Pain 1 D059350 ClinicalTrials
Amblyopia 1 D000550 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Narcolepsy 1 D009290 ClinicalTrials
Colitis, Ulcerative 1 D003093 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Endotoxemia 1 D019446 ClinicalTrials
Amyotrophic Lateral Sclerosis 1 D000690 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Alcoholism 1 D000437 ClinicalTrials
Mitochondrial Diseases 1 D028361 ClinicalTrials

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Cross References

Resources Reference
CAS NUMBER 58-08-2
ChEBI 27732
ChEMBL CHEMBL113
DrugBank DB00201
DrugCentral 463
EPA CompTox DTXSID0020232
FDA SRS 3G6A5W338E
Human Metabolome Database HMDB01847
Guide to Pharmacology 407
KEGG C07481
PDB CFF
PharmGKB PA448710
PubChem 2519
SureChEMBL SCHEMBL5671
ZINC ZINC000000001084
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