ADENOSINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1989)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C01EB10
UNII: K72T3FS567

Structure
InChI Key OIRDTQYFTABQOQ-KQYNXXCUSA-N
Smile Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H13N5O4
Molecular Weight 267.25
AlogP -1.98
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 139.54
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 19.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Adenosine receptor agonist
Primary Target
A1 receptor
A2A receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - 2180000
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKA family
- 160000-1100000 - 15000 -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC alpha subfamily
- 278000 - - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family
- 116000 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase CDC2 subfamily
- - 184000 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase MLK family TKL protein kinase TAK1 subfamily
- - 4400-34000 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 195000 - - -
Enzyme Kinase Protein kinase regulatory subunit
- 160000-1100000 - 15000 -
Enzyme Oxidoreductase
- 35000-35000000 - - -
Enzyme Transferase
- 495000-495000 - 580000-82000000 13.7-31.99
Enzyme
- 495000-495000 4400-34000 580000-82000000 13.7-31.99
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -18.7-2.55
Epigenetic regulator Writer Protein methyltransferase
- 100000 - - 26
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
39-2511.89 1.148 17.3 5.1-29000 10
Other cytosolic protein
- - 110000-112201.85 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 180.3
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC28 and SLC29 families of nucleoside transporters SLC28 Na+-coupled nucleoside transport family
- 3300 - 1800 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC28 and SLC29 families of nucleoside transporters SLC29 Facilitative nucleoside transporter family
63000 106000 - 106000 -
Unclassified protein
- 495000-495000 117000 - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 3 D009369 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Angina, Stable 3 D060050 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Coronary Stenosis 3 D023921 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Tachycardia, Ventricular 3 D017180 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Cardiomyopathies 2 D009202 ClinicalTrials
ST Elevation Myocardial Infarction 2 D000072657 ClinicalTrials
Pain 2 D010146 ClinicalTrials
Coronary Disease 2 D003327 ClinicalTrials
Takotsubo Cardiomyopathy 2 D054549 ClinicalTrials
Respiratory Distress Syndrome 2 D012128 ClinicalTrials
Leukemia 1 D007938 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Inflammation 1 D007249 ClinicalTrials
Ischemia 1 D007511 ClinicalTrials

Related Entries

MCS

Scaffolds

UNKNOWN
UNKNOWN
UNKNOWN
UNKNOWN

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Cardiac disorders
25.83
Injury, poisoning and procedural complications
11.95
General disorders and administration site conditions
11.6
Immune system disorders
10.72
Vascular disorders
10.72
Respiratory, thoracic and mediastinal disorders
8.79
Nervous system disorders
5.62
Investigations
3.34
Skin and subcutaneous tissue disorders
2.64
Gastrointestinal disorders
2.46

Cross References

Resources Reference
CAS NUMBER 58-61-7
ChEBI 16335
ChEMBL CHEMBL477
DrugBank DB00640
DrugCentral 90
EPA CompTox DTXSID1022558
FDA SRS K72T3FS567
Human Metabolome Database HMDB0000050
Guide to Pharmacology 2844
KEGG C00212
PDB ADN
PharmGKB PA448049
PubChem 60961
SureChEMBL SCHEMBL731
ZINC ZINC000002169830
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