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

ID: ALA4582146

PubChem CID: 155562055

Max Phase: Preclinical

Molecular Formula: C23H33Cl2N3O

Molecular Weight: 438.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCN1CCN(C(=O)Cc2ccc(Cl)c(Cl)c2)[C@@H]2[C@@H](N3CCCC3)CCC[C@@H]21

Standard InChI:  InChI=1S/C23H33Cl2N3O/c1-2-10-26-13-14-28(22(29)16-17-8-9-18(24)19(25)15-17)23-20(26)6-5-7-21(23)27-11-3-4-12-27/h8-9,15,20-21,23H,2-7,10-14,16H2,1H3/t20-,21-,23-/m0/s1

Standard InChI Key:  USWUHUMBTVHBPD-FUDKSRODSA-N

Molfile:  

 
     RDKit          2D

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   22.4259  -15.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0914  -16.1952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7493  -15.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4893  -14.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6730  -14.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1120  -18.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8173  -18.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8173  -17.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1120  -17.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4067  -18.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4067  -17.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7029  -17.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9946  -17.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9946  -18.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7029  -18.8761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7041  -16.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7041  -19.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9969  -16.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4123  -16.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9980  -15.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7069  -14.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7083  -13.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0007  -13.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2900  -13.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2920  -14.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5814  -13.5696    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.0007  -12.7475    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.4026  -19.2824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.4026  -16.8308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.9969  -20.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9981  -20.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9  2  1  1
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 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4582146

   ---

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: 438.44

Molecular Weight (Monoisotopic): 437.2001

AlogP: 4.48

#Rotatable Bonds: 5

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: 9.39

CX LogP: 4.64

CX LogD: 2.61

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -0.68

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