Details of the Drug

General Information of Drug (ID: DMZ0TGY)

Drug Name

CGS 21680

Synonyms

2-(4-(2-Carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine; Cgs 21680; CGS-21680; 120225-54-9; UNII-T5HB1E831H; T5HB1E831H; CHEMBL331372; CGS21680; 4-(2-((6-Amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)benzenepropanoic acid; CHEBI:73283; CGS 21680 hydrochloride; Benzenepropanoic acid, 4-(2-((6-amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)-; 2-[p-(2-Carboxyethyl)phenylethyl-Amino]-5'-N-Ethylcarboxamido Adenosine; [3H]CGS 21680

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

499.5

Logarithm of the Partition Coefficient (xlogp)

0.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C23H29N7O6
IUPAC Name: 3-[4-[2-[[6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]amino]ethyl]phenyl]propanoic acid
Canonical SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)NCCC4=CC=C(C=C4)CCC(=O)O)N)O)O
InChI: InChI=1S/C23H29N7O6/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29)/t16-,17+,18-,22+/m0/s1
InChIKey: PAOANWZGLPPROA-RQXXJAGISA-N

Cross-matching ID

PubChem CID: 3086599
ChEBI ID: CHEBI:73283
CAS Number: 120225-54-9
TTD ID: D0J2UW

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adenosine A2a receptor (ADORA2A)	TTM2AOE	AA2AR_HUMAN	Agonist	[2]
Adenosine A2b receptor (ADORA2B)	TTNE7KG	AA2BR_HUMAN	Agonist	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[4]
Basic helix-loop-helix ARNT-like protein 1 (BMAL1)	OTMI12L2	BMAL1_HUMAN	Gene/Protein Processing	[5]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Protein Interaction/Cellular Processes	[6]
Circadian locomoter output cycles protein kaput (CLOCK)	OTNEOJY7	CLOCK_HUMAN	Gene/Protein Processing	[5]
Collagen alpha-1(III) chain (COL3A1)	OTT1EMLM	CO3A1_HUMAN	Gene/Protein Processing	[6]
Matrix metalloproteinase-14 (MMP14)	OT9C197Z	MMP14_HUMAN	Gene/Protein Processing	[4]
Matrix metalloproteinase-9 (MMP9)	OTB2QDAV	MMP9_HUMAN	Gene/Protein Processing	[4]
Nuclear receptor subfamily 1 group D member 1 (NR1D1)	OTJ38PTB	NR1D1_HUMAN	Gene/Protein Processing	[5]
Period circadian protein homolog 2 (PER2)	OTU2B1DJ	PER2_HUMAN	Gene/Protein Processing	[5]
Vascular endothelial growth factor A, long form	OTIM9MZ3	VEGFA_HUMAN	Protein Interaction/Cellular Processes	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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: 424).
2	Effects of CGS 21680, a selective adenosine A2A receptor agonist, on allergic airways inflammation in the rat. Eur J Pharmacol. 2002 Mar 8;438(3):183-8.
3	[3H]CGS 21680, a selective A2 adenosine receptor agonist directly labels A2 receptors in rat brain. J Pharmacol Exp Ther. 1989 Dec;251(3):888-93.
4	Adenosine A(2A) receptors play a role in the pathogenesis of hepatic cirrhosis. Br J Pharmacol. 2006 Aug;148(8):1144-55. doi: 10.1038/sj.bjp.0706812. Epub 2006 Jun 19.
5	Adenosine A2A receptor and TNF- regulate the circadian machinery of the human monocytic THP-1 cells. Inflammation. 2013 Feb;36(1):152-62. doi: 10.1007/s10753-012-9530-x.
6	Adenosine A(2A) receptor promotes collagen type III synthesis via -catenin activation in human dermal fibroblasts. Br J Pharmacol. 2016 Dec;173(23):3279-3291. doi: 10.1111/bph.13615. Epub 2016 Oct 4.
7	Adenosine up-regulates vascular endothelial growth factor in human macrophages. Biochem Biophys Res Commun. 2010 Feb 12;392(3):351-6. doi: 10.1016/j.bbrc.2010.01.023. Epub 2010 Jan 11.