((3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl)((3S,4R,5R)-4-(4-chlorophenyl)-4-hydroxy-3,5-dimethylpiperidin-1-yl)methanone

ID: ALA1091150

PubChem CID: 46885711

Max Phase: Preclinical

Molecular Formula: C28H35ClF2N2O2

Molecular Weight: 505.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CN(C(=O)[C@@H]2CN(C(C)(C)C)C[C@H]2c2ccc(F)cc2F)C[C@H](C)[C@@]1(O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C28H35ClF2N2O2/c1-17-13-32(14-18(2)28(17,35)19-6-8-20(29)9-7-19)26(34)24-16-33(27(3,4)5)15-23(24)22-11-10-21(30)12-25(22)31/h6-12,17-18,23-24,35H,13-16H2,1-5H3/t17-,18+,23-,24+,28-/m0/s1

Standard InChI Key:  GXEILWZMBSGTIK-XYLBCIRHSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
    7.5891   -6.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741   -6.4680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9230   -5.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6390   -5.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8143   -5.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3980   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8068   -3.7834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5730   -4.5043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0958   -4.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9218   -4.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3385   -3.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9303   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1010   -3.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6880   -3.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3049   -7.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6063   -7.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0342   -7.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3000   -8.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3293   -5.2220    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3461   -2.3631    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1580   -3.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3366   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9239   -4.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3389   -5.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665   -5.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3333   -3.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -5.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -5.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6638   -6.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930   -6.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089   -5.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231   -3.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -6.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450   -7.3411    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0
  3  4  1  0
 15 18  1  0
  4  5  1  0
 10 19  1  0
  9 10  2  0
 12 20  1  0
  8 21  1  0
  5  1  1  0
 10 11  1  0
  1  2  1  0
 11 12  2  0
  8 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 12 13  1  0
 23 26  1  1
  2  3  1  0
 23 27  1  0
 13 14  2  0
 27 28  2  0
 14  9  1  0
 28 29  1  0
  4  9  1  6
 29 30  2  0
  6  7  2  0
 30 31  1  0
  2 15  1  0
 31 32  2  0
 32 27  1  0
  6  8  1  0
 22 33  1  1
 15 16  1  0
 24 34  1  1
  5  6  1  1
 30 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091150

   ((3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl)((3S,4R,5R)-4-(4-chlorophenyl)-4-hydroxy-3,5-dimethylpiperidin-1-yl)methanone

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: 505.05

Molecular Weight (Monoisotopic): 504.2355

AlogP: 5.43

#Rotatable Bonds: 3

Polar Surface Area: 43.78

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.61

CX Basic pKa: 9.05

CX LogP: 4.98

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.61

Np Likeness Score: -0.56

References

1. Lansdell MI, Hepworth D, Calabrese A, Brown AD, Blagg J, Burring DJ, Wilson P, Fradet D, Brown TB, Quinton F, Mistry N, Tang K, Mount N, Stacey P, Edmunds N, Adams C, Gaboardi S, Neal-Morgan S, Wayman C, Cole S, Phipps J, Lewis M, Verrier H, Gillon V, Feeder N, Heatherington A, Sultana S, Haughie S, Martin SW, Sudworth M, Tweedy S..  (2010)  Discovery of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans.,  53  (8): [PMID:20329799] [10.1021/jm9017866]

Source

Source(1):

• Scientific Literature