(2S,4S)-4-nitrophenethyl 1-(2-chlorobenzyl)-4-(4-methoxybenzylamino)pyrrolidine-2-carboxylate

ID: ALA4780551

PubChem CID: 162663612

Max Phase: Preclinical

Molecular Formula: C28H30ClN3O5

Molecular Weight: 524.02

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(CN[C@H]2C[C@@H](C(=O)OCCc3ccc([N+](=O)[O-])cc3)N(Cc3ccccc3Cl)C2)cc1

Standard InChI:  InChI=1S/C28H30ClN3O5/c1-36-25-12-8-21(9-13-25)17-30-23-16-27(31(19-23)18-22-4-2-3-5-26(22)29)28(33)37-15-14-20-6-10-24(11-7-20)32(34)35/h2-13,23,27,30H,14-19H2,1H3/t23-,27-/m0/s1

Standard InChI Key:  HOWXFCDKOQOSKZ-HOFKKMOUSA-N

Molfile:  

 
     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   10.3033  -11.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1283  -11.3366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3851  -10.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7158  -10.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0509  -10.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2662  -10.2980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0943   -9.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3096   -9.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1430   -8.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3591   -8.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7453   -8.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9207   -9.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7043   -9.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9603   -8.4760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7873   -7.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6124  -12.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2760  -12.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4544  -12.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1180  -13.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6023  -14.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4267  -14.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7594  -13.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1734  -10.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7857  -10.8497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3460   -9.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5706  -10.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1829  -11.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9677  -10.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5795  -13.3304    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.9877   -9.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1834  -10.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5567  -11.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3611  -11.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5766  -10.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3811  -10.2481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5966   -9.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9700  -10.8371    0.0000 O   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
  5  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  1  0
 23 25  2  0
  3 23  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 22 29  1  0
 31 28  2  0
 28 32  1  0
 30 31  1  0
 32 33  2  0
 33 34  1  0
 30 34  2  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
M  CHG  2  35   1  37  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4780551

   ---

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: 524.02

Molecular Weight (Monoisotopic): 523.1874

AlogP: 4.78

#Rotatable Bonds: 11

Polar Surface Area: 93.94

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.39

CX LogP: 5.46

CX LogD: 4.43

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.22

Np Likeness Score: -1.19

References

1. Nguyen T,Marusich J,Li JX,Zhang Y.  (2020)  Neuropeptide FF and Its Receptors: Therapeutic Applications and Ligand Development.,  63  (21.0): [PMID:32673481] [10.1021/acs.jmedchem.0c00643]

Source

Source(1):

• Scientific Literature