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

ID: ALA4467644

PubChem CID: 155532812

Max Phase: Preclinical

Molecular Formula: C22H31Cl2N3O

Molecular Weight: 424.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1CCN(C(=O)Cc2ccc(Cl)c(Cl)c2)[C@H]2[C@@H]1CCC[C@@H]2N1CCCC1

Standard InChI:  InChI=1S/C22H31Cl2N3O/c1-2-25-12-13-27(21(28)15-16-8-9-17(23)18(24)14-16)22-19(25)6-5-7-20(22)26-10-3-4-11-26/h8-9,14,19-20,22H,2-7,10-13,15H2,1H3/t19-,20-,22-/m0/s1

Standard InChI Key:  IPKVFDXSTVEXOJ-ONTIZHBOSA-N

Molfile:  

 
     RDKit          2D

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   22.5250   -4.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1904   -4.9403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8484   -4.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5884   -3.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7721   -3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2111   -7.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9163   -7.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9163   -6.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2111   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5058   -7.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5058   -6.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8020   -5.9867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0937   -6.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0937   -7.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8020   -7.6211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8031   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8031   -8.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0960   -4.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5114   -4.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0971   -3.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8059   -3.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8074   -2.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0997   -2.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3891   -2.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3911   -3.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6805   -2.3146    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0998   -1.4925    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.5017   -8.0275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.5017   -5.5759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.0960   -8.8479    0.0000 C   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
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 12 13  1  0
 13 14  1  0
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 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
 17 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4467644

   ---

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: 424.42

Molecular Weight (Monoisotopic): 423.1844

AlogP: 4.09

#Rotatable Bonds: 4

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: 9.37

CX LogP: 4.12

CX LogD: 2.13

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -0.58

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