Compound: Cgs 21680
SMILES: O=C(NCC)[C@H]1O[C@@H](n2c3nc(nc(c3nc2)N)NCCc4ccc(CCC(=O)O)cc4)[C@@H]([C@@H]1O)O
InChIKey: PAOANWZGLPPROA-RQXXJAGISA-N
Synonyms: Cgs 21680, 120225-54-9, CGS-21680, 2-(4-(2-Carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine, CGS21680, T5HB1E831H, 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, DTXSID6043882, 4-(2-((6-Amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)benzenepropanoic acid, 4-[2-[[6-Amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid, CHEBI:73283, Benzenepropanoic acid, 4-(2-((6-amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl)amino)ethyl)-, 3-(4-(2-((6-Amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)amino)ethyl)phenyl)propanoic acid, 3-{4-[2-({6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl]-9H-purin-2-yl}amino)ethyl]phenyl}propanoic acid, 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, Benzenepropanoic acid, 4-[2-[[6-amino-9-(N-ethyl-beta-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]-, RefChem:918329, DTXCID4023882, 124182-57-6, CHEMBL331372, 4-[2-[[6-Amino-9-(N-ethyl-b-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid, C23H29N7O6, 2-[p-(2-Carboxyethyl)phenylethyl-Amino]-5'-N-Ethylcarboxamido Adenosine, PAOANWZGLPPROA-RQXXJAGISA-N, UNII-T5HB1E831H, NGI, [3H]-CGS21680, [3H]CGS 21680, GTPL375, GTPL424, SCHEMBL724684, orb1685664, BDBM35804, EX-A2473A, AKOS030530328, [3H]-CGS 21680, CS-0424, NCGC00024976-02, NCGC00024976-03, NCGC00024976-06, NCGC00024976-10, 3-{4-[2-({6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}amino)ethyl]phenyl}propanoic acid, BS-14476, DA-72130, HY-13201, C71688, Q5010992, 2-p-(2-carboxyethyl)phenethylamino-5''''''''-N-ethylcarboxamidoadenosine, 2-(4-(2-CARBOXYETHYL)PHENETHYLAMINO)-5'-N- ETHYLCARBOXAMIDOADENOSINE, 2-[4-(2-carboxyethyl)-phenethylamino]-5''''''''-N-ethylcarboxamidoadenosine, 2-[4-(2-carboxyethyl)phenethylamino]-5''''''''-N-ethylcarboxamidoadenosine, (CGS21680) 3-(4-{2-[6-Amino-9-(5-ethylcarbamoylmethyl-3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-ylamino]-ethyl}-phenyl)-propionic acid, 3-(4-(2-(6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxy-tetrahydrofuran-2-yl)-9H-purin-2-ylamino)ethyl)phenyl)propanoic acid, 3-(4-(2-(6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-ylamino)ethyl)phenyl)propanoic acid, 3-(4-{2-[6-Amino-9-((2R,3R,4S,5S)-5-ethylcarbamoyl-3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-ylamino]-ethyl}-phenyl)-propionic acid, 3-[4-[2-[[6-amino-9-[(2r,3r,4s,5s)-5-(ethylcarbamoyl)-3,4-dihydroxy-oxolan-2-yl]purin-2-yl]amino]ethyl]phenyl]propanoic acid, 3-[4-[2-[[6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxy-tetrahydrofuran-2-yl]purin-2-yl]amino]ethyl]phenyl]propanoic acid, 3-[4-[2-[[6-Amino-9-[(3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxy-oxolan-2-yl]purin-2-yl]amino]ethyl]phenyl]propanoic acid hydrochloride, 4-[2-[[6-Amino-9-(N-ethyl-|_-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid, 4-[2-[[6-Amino-9-(N-ethyl-|A-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid, BENZENEPROPANOIC ACID, 4-(2-((6-AMINO-9-(N-ETHYL-.BETA.-D-RIBOFURANURONAMIDOSYL)-9H-PURIN-2-YL)AMINO)ETHYL)-
Theoretical properties:
molecular_formula: C23H29N7O6
molecular_weight: 499.5 g/mol
exact_mass: 499.21793167 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 10
heavy_atom_count: 36
topological_polar_surface_area: 198 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: CGS-21680 is a derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and the hydrogen at position 2 on the adenine is replaced by a 4-(2-carboxyethyl)phenethylamino group. It has a role as an anti-inflammatory agent and an adenosine A2A receptor agonist. It is a member of adenosines, a monocarboxylic acid and a dicarboxylic acid monoamide. It is functionally related to an adenosine.
chebi: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by <em>N</em>-ethylcarboxamido and the hydrogen at position 2 on the adenine is replaced by a 4-(2-carboxyethyl)phenethylamino group.
chembl: CGS-21680 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: CGS-21680 is a specific adenosine A2A subtype receptor agonist. It is usually presented as an organic hydrochloride salt with a molecular weight of 536.0 g/M. It is soluble up to 3.4 mg/mL in DMSO and 20 mg/mL in 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin.
The chemical is currently used by researchers interested in studying neuronal transmission with a high-affinity, subtype specific analogue for adenosine. This includes research in respiration where it is believed that A2A receptors are involved in rhythm generation in the pre-Bötzinger complex. The drug is not currently approved for use in a therapeutic capacity.