Details of the Drug

General Information of Drug (ID: DMAO9SH)

Drug Name
[3H]NECA
Synonyms
5'-N-Ethylcarboxamidoadenosine; NECA; 35920-39-9; Adenosine-5'-(N-ethylcarboxamide); N-ethyl-5'-carboxamidoadenosine; 1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-beta-D-ribofuranuronamide; N-ETHYL-5'-CARBOXAMIDO ADENOSINE; MLS000069759; CHEMBL464859; CHEBI:73284; 5'-N-ETHYLCARBOXAMIDO-ADENOSINE; SMR000058759; N-Ethylcarboxamidoadenosine; 5'-N(Sup 6)-Ethylcarboxamidoadenosine; (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide; [3H]adenosine-5'-(N-ethylcarboxamide)
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 308.29
Logarithm of the Partition Coefficient (xlogp) -0.7
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C12H16N6O4
IUPAC Name
(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
Canonical SMILES
CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
InChI
InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/m0/s1
InChIKey
JADDQZYHOWSFJD-FLNNQWSLSA-N
Cross-matching ID
PubChem CID
448222
ChEBI ID
CHEBI:73284
CAS Number
35920-39-9
DrugBank ID
DB03719
TTD ID
D0K8ZZ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Inhibitor [2]
Adenosine A2a receptor (ADORA2A) TTM2AOE AA2AR_HUMAN Inhibitor [2]
Adenosine A2b receptor (ADORA2B) TTNE7KG AA2BR_HUMAN Agonist [3]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Agonist [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Adenosine receptor A3 (ADORA3) OTHO1BLK AA3R_HUMAN Protein Interaction/Cellular Processes [5]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Protein Interaction/Cellular Processes [6]
Interleukin-13 (IL13) OTI4YS3Y IL13_HUMAN Protein Interaction/Cellular Processes [6]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 425).
2 Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives. J Med Chem. 1988 Jun;31(6):1179-83.
3 Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):1-9.
4 Inhibition of human mast cell activation with the novel selective adenosine A(2B) receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX)(2). Biochem Pharmacol. 2001 Nov 1;62(9):1163-73.
5 Pyrimidine derivatives as potent and selective A3 adenosine receptor antagonists. J Med Chem. 2011 Jan 27;54(2):457-71. doi: 10.1021/jm100843z. Epub 2010 Dec 27.
6 Adenosine deaminase 1 and concentrative nucleoside transporters 2 and 3 regulate adenosine on the apical surface of human airway epithelia: implications for inflammatory lung diseases. Biochemistry. 2007 Sep 11;46(36):10373-83. doi: 10.1021/bi7009647. Epub 2007 Aug 15.
7 Inhibitory effects of benzodiazepines on the adenosine A(2B) receptor mediated secretion of interleukin-8 in human mast cells. Eur J Pharmacol. 2013 Jan 30;700(1-3):152-8. doi: 10.1016/j.ejphar.2012.12.003. Epub 2012 Dec 22.