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

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ChEBI Name (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol
ChEBI ID CHEBI:64080
ChEBI ASCII Name (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H27NO3
Net Charge 0
Average Mass 329.43330
Monoisotopic Mass 329.19909
InChI InChI=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
InChIKey QLJOSZATCBCBDR-DFKUFRTHSA-N
SMILES NC[C@@H]1O[C@@H](Cc2c(O)c(O)ccc12)C12CC3CC(CC(C3)C1)C2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): dopamine agonist
A drug that binds to and activates dopamine receptors.
Application(s): antiparkinson drug
A drug used in the treatment of Parkinson's disease.
dopamine agonist
A drug that binds to and activates dopamine receptors.
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ChEBI Ontology
Outgoing (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 (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 Sources
A 77636 ChEBI
A-77636 ChEBI
A77636 ChEBI
Manual Xrefs Databases
EP870757 Patent
LSM-20969 LINCS
US6057364 Patent
View more database links
Registry Number Type Source
5855679 Reaxys Registry Number Reaxys
Last Modified
25 February 2016