(4R)-4-[[(5-chloro-8-quinolyl)methylamino]methyl]-1-cyclopropyl-pyrrolidin-2-one

ID: ALA5094012

PubChem CID: 166635852

Max Phase: Preclinical

Molecular Formula: C18H20ClN3O

Molecular Weight: 329.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C[C@H](CNCc2ccc(Cl)c3cccnc23)CN1C1CC1

Standard InChI:  InChI=1S/C18H20ClN3O/c19-16-6-3-13(18-15(16)2-1-7-21-18)10-20-9-12-8-17(23)22(11-12)14-4-5-14/h1-3,6-7,12,14,20H,4-5,8-11H2/t12-/m1/s1

Standard InChI Key:  RMLDETFEMQHVSC-GFCCVEGCSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.8489    0.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224    0.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1325   -0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8489   -0.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -1.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8399   -2.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5536   -1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635   -0.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5631    0.7973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058   -0.4397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201   -0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5203    0.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    0.5513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7388   -0.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872   -0.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -0.1624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390    1.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545    1.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7399    2.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  5  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  6 10  1  0
  1 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  6
 16 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 18 20  2  0
 21 17  1  0
 21 22  1  0
 21 23  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5094012

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 329.83

Molecular Weight (Monoisotopic): 329.1295

AlogP: 2.99

#Rotatable Bonds: 5

Polar Surface Area: 45.23

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.57

CX LogP: 1.89

CX LogD: -0.25

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: -1.26

References

1. Levit Kaplan A, Strachan RT, Braz JM, Craik V, Slocum S, Mangano T, Amabo V, O'Donnell H, Lak P, Basbaum AI, Roth BL, Shoichet BK..  (2022)  Structure-Based Design of a Chemical Probe Set for the 5-HT_5A Serotonin Receptor.,  65  (5.0): [PMID:35195401] [10.1021/acs.jmedchem.1c02031]

Source

Source(1):

• Scientific Literature