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CHEBI:64080 - (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol

Default Structure
ChEBI IDCHEBI:64080
ChEBI Name(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol
Stars
ASCII Name(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol
DefinitionAn isochromene that is 3,4-dihydroisochromene-5,6-diol bearing additional aminomethyl and 1-adamantyl substituents at positions 1 and 3 respectively (the 1R,3S-diastereomer). Potent and selective dopamine D1-like receptor agonist (pEC50 values are 8.97 and < 5 for D1-like and D2-like receptors respectively). Displays anti-Parkinsonian activity following oral administration in vivo.
Last Modified25 February 2016
SubmitterSteve
DownloadsMolfile
FormulaC20H27NO3
Net Charge0
Average Mass329.440
Monoisotopic Mass329.19909
SMILESNC[C@@H]1O[C@H](C23CC4CC(CC(C4)C2)C3)Cc2c1ccc(O)c2O
InChIInChI=1S/C20H27NO3/c21-10-17-14-1-2-16(22)19(23)15(14)6-18(24-17)20-7-11-3-12(8-20)5-13(4-11)9-20/h1-2,11-13,17-18,22-23H,3-10,21H2/t11?,12?,13?,17-,18-,20?/m0/s1
InChIKeyQLJOSZATCBCBDR-DFKUFRTHSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
dopamine agonist  A drug that binds to and activates dopamine receptors.
Applications:
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
dopamine agonist  A drug that binds to and activates dopamine receptors.
ChEBI Ontology
Outgoing Relation(s)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) has role antiparkinson drug (CHEBI:48407)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) has role dopamine agonist (CHEBI:51065)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) is a adamantanes (CHEBI:51339)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) is a catechols (CHEBI:33566)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) is a isochromenes (CHEBI:38761)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) is a primary amino compound (CHEBI:50994)
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080) is conjugate base of (1R,3S)-3-(adamantan-1-yl)-1-(ammoniomethyl)-3,4-dihydroisochromene-5,6-diol(1+) (CHEBI:64079)
Incoming Relation(s)
(1R,3S)-3-(adamantan-1-yl)-1-(ammoniomethyl)-3,4-dihydroisochromene-5,6-diol(1+) (CHEBI:64079) is conjugate acid of (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol (CHEBI:64080)
IUPAC Name 
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydro-1H-isochromene-5,6-diol
Synonyms  Source
A 77636ChEBI
A-77636ChEBI
A77636ChEBI
Manual XrefsDatabases
EP870757Patent
LSM-20969LINCS
US6057364Patent
Registry NumbersSources
Reaxys:5855679Reaxys