2-(3,4-Dichlorophenyl)-1-[(4aSR,8SR,8aSR)-4-methyl-8-(pyrrolidin-1-yl)-3,4,4a,5,6,7,8,8a-octahydroquinoxalin-1(2H)-yl]ethan-1-one

ID: ALA4462000

PubChem CID: 155529017

Max Phase: Preclinical

Molecular Formula: C21H29Cl2N3O

Molecular Weight: 410.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(C(=O)Cc2ccc(Cl)c(Cl)c2)[C@H]2[C@@H]1CCC[C@@H]2N1CCCC1

Standard InChI:  InChI=1S/C21H29Cl2N3O/c1-24-11-12-26(20(27)14-15-7-8-16(22)17(23)13-15)21-18(24)5-4-6-19(21)25-9-2-3-10-25/h7-8,13,18-19,21H,2-6,9-12,14H2,1H3/t18-,19-,21-/m0/s1

Standard InChI Key:  CQXHKVAZLJKFTQ-ZJOUEHCJSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   15.8554  -15.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5208  -15.7866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1788  -15.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9188  -14.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1025  -14.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5415  -18.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2467  -18.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2467  -17.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5415  -16.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8362  -18.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8362  -17.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1324  -16.8331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4241  -17.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4241  -18.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1324  -18.4675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1335  -16.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1335  -19.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4264  -15.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8418  -15.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4275  -14.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1363  -14.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1378  -13.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4301  -13.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7195  -13.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7215  -14.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0109  -13.1610    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.4302  -12.3389    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.8320  -18.8738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8320  -16.4222    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
 11  9  1  0
 10  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 15 17  1  0
 16 18  1  0
  9  2  1  1
 16 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 23 27  1  0
 10 28  1  1
 11 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4462000

   ---

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: 410.39

Molecular Weight (Monoisotopic): 409.1688

AlogP: 3.70

#Rotatable Bonds: 3

Polar Surface Area: 26.79

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.44

CX LogP: 3.76

CX LogD: 1.72

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.57

References

1. Tangherlini G, Kalinin DV, Schepmann D, Che T, Mykicki N, Ständer S, Loser K, Wünsch B..  (2019)  Development of Novel Quinoxaline-Based κ-Opioid Receptor Agonists for the Treatment of Neuroinflammation.,  62  (2): [PMID:30543421] [10.1021/acs.jmedchem.8b01609]

Source

Source(1):

• Scientific Literature