Marvin  03021214042D          

 24 28  0  0  1  0            999 V2000
   12.5013   -7.3141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3977   -5.2151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561   -6.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0479   -8.9402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2364   -6.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5144   -6.4902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9849   -6.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7802   -6.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2315   -5.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0871   -6.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6970   -6.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5336   -6.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9792   -4.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0760   -7.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8106   -6.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7824   -7.7130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3387   -6.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7014   -5.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5363   -5.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3831   -6.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3568   -7.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6635   -6.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6483   -7.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7693   -8.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 16  1  0  0  0  0
  2 20  1  0  0  0  0
  3 22  1  0  0  0  0
  4 24  1  0  0  0  0
  6  5  1  1  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 10 20  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 17  1  0  0  0  0
 12 19  1  0  0  0  0
 13 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 16  1  0  0  0  0
 14 21  1  0  0  0  0
 16 24  1  1  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <ID>
CHEBI:64080

> <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.

> <STAR>
3

> <SYNONYM>
A77636; A-77636; A 77636

> <IUPAC_NAME>
(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydro-1H-isochromene-5,6-diol

> <FORMULA>
C20H27NO3

> <MASS>
329.43330

> <MONOISOTOPIC_MASS>
329.19909

> <CHARGE>
0

> <SMILES>
NC[C@@H]1O[C@@H](Cc2c(O)c(O)ccc12)C12CC3CC(CC(C3)C1)C2

> <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

> <REAXYS_REGISTRY_NUMBER>
5855679

> <LINCS_ACCESSION>
LSM-20969

$$$$