ID: ALA269004

Max Phase: Preclinical

Molecular Formula: C16H25NO

Molecular Weight: 247.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCN(CCC)[C@H]1CCc2c(O)cccc2C1

Standard InChI:  InChI=1S/C16H25NO/c1-3-10-17(11-4-2)14-8-9-15-13(12-14)6-5-7-16(15)18/h5-7,14,18H,3-4,8-12H2,1-2H3/t14-/m0/s1

Standard InChI Key:  MDBWEQVKJDMEMK-AWEZNQCLSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 247.38

Molecular Weight (Monoisotopic): 247.1936

AlogP: 3.37

#Rotatable Bonds: 5

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.03

CX Basic pKa: 11.02

CX LogP: 3.27

CX LogD: 1.14

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -0.22

References

1. Johansson AM, Nilsson JL, Karlén A, Hacksell U, Svensson K, Carlsson A, Kenne L, Sundell S..  (1987)  C3-methylated 5-hydroxy-2-(dipropylamino)tetralins: conformational and steric parameters of importance for central dopamine receptor activation.,  30  (7): [PMID:3599021] [10.1021/jm00390a004]

2. van Vliet LA, Tepper PG, Dijkstra D, Damsma G, Wikström H, Pugsley TA, Akunne HC, Heffner TG, Glase SA, Wise LD..  (1996)  Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins. Relevance of D2 agonist binding for determination of receptor subtype selectivity.,  39  (21): [PMID:8863800] [10.1021/jm960345l]

3. Johnson M, Antonio T, Reith ME, Dutta AK..  (2012)  Structure-activity relationship study of N⁶-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N⁶-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine analogues: development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization.,  55  (12): [PMID:22642365] [10.1021/jm300268s]

4. Gogoi S, Biswas S, Modi G, Antonio T, Reith ME, Dutta AK..  (2012)  Novel bivalent ligands for D2/D3 dopamine receptors: Significant co-operative gain in D2 affinity and potency.,  3  (12): [PMID:23275802] [10.1021/ml3002117]

5. Gopishetty B, Zhang S, Kharkar PS, Antonio T, Reith M, Dutta AK..  (2013)  Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: impact on functional activity and selectivity for dopamine D2/D3 receptors.,  21  (11): [PMID:23623679] [10.1016/j.bmc.2013.03.059]

6. Das B, Vedachalam S, Luo D, Antonio T, Reith ME, Dutta AK..  (2015)  Development of a Highly Potent D2/D3 Agonist and a Partial Agonist from Structure-Activity Relationship Study of N(6)-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N(6)-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Analogues: Implication in the Treatment of Parkinson's Disease.,  58  (23): [PMID:26555041] [10.1021/acs.jmedchem.5b01031]

7. Weichert D, Stanek M, Hübner H, Gmeiner P..  (2016)  Structure-guided development of dual β2 adrenergic/dopamine D2 receptor agonists.,  24  (12): [PMID:27132867] [10.1016/j.bmc.2016.04.028]

8. Dinda B, Das B, Biswas S, Sharma H, Armstrong C, Yedlapudi D, Antonio T, Reith M, Dutta AK..  (2023)  Bivalent dopamine agonists with co-operative binding and functional activities at dopamine D2 receptors, modulate aggregation and toxicity of alpha synuclein protein.,  78  [PMID:36571976] [10.1016/j.bmc.2022.117131]

Source

Source(1):

• Scientific Literature