(4aR,5S,8aS)-Methyl 4-(2-(3-Chloro-4-fluorophenyl)acetyl)-5-((S)-3-hydroxypyrrolidin-1-yl)octahydroquinoxaline-1(2H)-carboxylate

ID: ALA4061582

PubChem CID: 137638013

Max Phase: Preclinical

Molecular Formula: C22H29ClFN3O4

Molecular Weight: 453.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)N1CCN(C(=O)Cc2ccc(F)c(Cl)c2)[C@@H]2[C@@H](N3CC[C@H](O)C3)CCC[C@@H]21

Standard InChI:  InChI=1S/C22H29ClFN3O4/c1-31-22(30)26-9-10-27(20(29)12-14-5-6-17(24)16(23)11-14)21-18(3-2-4-19(21)26)25-8-7-15(28)13-25/h5-6,11,15,18-19,21,28H,2-4,7-10,12-13H2,1H3/t15-,18-,19-,21+/m0/s1

Standard InChI Key:  XYUJCLASLNMYPP-LDBRAYGESA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   14.6350   -2.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9466   -3.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4391   -3.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6369   -3.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6118   -4.5386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9164   -4.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9470   -5.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6728   -6.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7033   -7.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4334   -7.3914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0080   -7.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2779   -7.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3724   -5.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0982   -6.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7979   -5.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7673   -4.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0373   -4.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3419   -4.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0055   -3.6572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6531   -3.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3668   -2.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5381   -2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3125   -3.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1449   -1.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8339   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0162   -0.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5105   -1.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8242   -2.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7018   -0.0288    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.6886   -1.3430    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.8281   -1.6788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3359   -4.0915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3652   -6.5749    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  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  5  1  0
 13 18  1  0
 17 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
  1 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28  1  1  0
 26 29  1  0
 27 30  1  0
 21 31  1  6
 18 32  1  1
 13 33  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4061582

   ---

2. Alternative Forms:

   

   ALA4061582

   ---

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: 453.94

Molecular Weight (Monoisotopic): 453.1831

AlogP: 2.29

#Rotatable Bonds: 3

Polar Surface Area: 73.32

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.50

CX LogP: 2.00

CX LogD: 0.87

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.76

Np Likeness Score: -0.57

References

1. Soeberdt M, Molenveld P, Storcken RP, Bouzanne des Mazery R, Sterk GJ, Autar R, Bolster MG, Wagner C, Aerts SN, van Holst FR, Wegert A, Tangherlini G, Frehland B, Schepmann D, Metze D, Lotts T, Knie U, Lin KY, Huang TY, Lai CC, Ständer S, Wünsch B, Abels C..  (2017)  Design and Synthesis of Enantiomerically Pure Decahydroquinoxalines as Potent and Selective κ-Opioid Receptor Agonists with Anti-Inflammatory Activity in Vivo.,  60  (6): [PMID:28218838] [10.1021/acs.jmedchem.6b01868]

Source

Source(1):

• Scientific Literature