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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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)

MIA Detail

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.