2-(2,6-dichlorophenyl)-1-((1S,3R)-3-(hydroxymethyl)-5-(2-hydroxypropan-2-yl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

ID: ALA3421730

Chembl Id: CHEMBL3421730

Cas Number: 1638667-81-8

PubChem CID: 117720272

Max Phase: Preclinical

Molecular Formula: C22H25Cl2NO3

Molecular Weight: 422.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1c2cccc(C(C)(C)O)c2C[C@H](CO)N1C(=O)Cc1c(Cl)cccc1Cl

Standard InChI:  InChI=1S/C22H25Cl2NO3/c1-13-15-6-4-7-18(22(2,3)28)16(15)10-14(12-26)25(13)21(27)11-17-19(23)8-5-9-20(17)24/h4-9,13-14,26,28H,10-12H2,1-3H3/t13-,14+/m0/s1

Standard InChI Key:  CWRORBWPLQQFMX-UONOGXRCSA-N

Alternative Forms

1. Parent:

   

   ALA3421730

   2-(2,6-dichlorophenyl)-1-((1S,3R)-3-(hydroxymethyl)-5-(2-hydroxypropan-2-yl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

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

Calculated Properties

Molecular Weight: 422.35

Molecular Weight (Monoisotopic): 421.1211

AlogP: 4.27

#Rotatable Bonds: 4

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: -0.26

References

1. Abdel-Magid AF..  (2015)  Allosteric modulators: an emerging concept in drug discovery.,  6  (2): [PMID:25699154] [10.1021/ml5005365]

2. Hao J, Beck JP, Schaus JM, Krushinski JH, Chen Q, Beadle CD, Vidal P, Reinhard MR, Dressman BA, Massey SM, Boulet SL, Cohen MP, Watson BM, Tupper D, Gardinier KM, Myers J, Johansson AM, Richardson J, Richards DS, Hembre EJ, Remick DM, Coates DA, Bhardwaj RM, Diseroad BA, Bender D, Stephenson G, Wolfangel CD, Diaz N, Getman BG, Wang XS, Heinz BA, Cramer JW, Zhou X, Maren DL, Falcone JF, Wright RA, Mitchell SN, Carter G, Yang CR, Bruns RF, Svensson KA..  (2019)  Synthesis and Pharmacological Characterization of 2-(2,6-Dichlorophenyl)-1-((1S,3R)-5-(3-hydroxy-3-methylbutyl)-3-(hydroxymethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one (LY3154207), a Potent, Subtype Selective, and Orally Available Positive Allosteric Modulator of the Human Dopamine D1 Receptor.,  62  (19): [PMID:31532644] [10.1021/acs.jmedchem.9b01234]

3. Hall A, Provins L, Valade A..  (2019)  Novel Strategies To Activate the Dopamine D₁ Receptor: Recent Advances in Orthosteric Agonism and Positive Allosteric Modulation.,  62  (1): [PMID:30525590] [10.1021/acs.jmedchem.8b01767]

Source

Source(1):

• Scientific Literature