(R)-N-(2-(1-(2-(1-(3-methylbenzoyl)piperidin-4-yl)ethyl)pyrrolidin-3-ylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide

ID: ALA1090548

PubChem CID: 46842086

Max Phase: Preclinical

Molecular Formula: C29H35F3N4O3

Molecular Weight: 544.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)N2CCC(CCN3CC[C@@H](NC(=O)CNC(=O)c4cccc(C(F)(F)F)c4)C3)CC2)c1

Standard InChI:  InChI=1S/C29H35F3N4O3/c1-20-4-2-6-23(16-20)28(39)36-14-9-21(10-15-36)8-12-35-13-11-25(19-35)34-26(37)18-33-27(38)22-5-3-7-24(17-22)29(30,31)32/h2-7,16-17,21,25H,8-15,18-19H2,1H3,(H,33,38)(H,34,37)/t25-/m1/s1

Standard InChI Key:  VVWKTZGDVFHHDW-RUZDIDTESA-N

Molfile:  

     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
   11.0673  -10.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0660  -11.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7790  -11.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4983  -11.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4951  -10.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7771   -9.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2061   -9.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9249  -10.2293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2027   -8.9948    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.9198   -9.4005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3500   -9.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3498   -9.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6375  -10.2396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9248   -9.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2077  -10.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4950   -9.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2080  -11.0650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781  -10.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -9.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213  -10.6644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0143  -11.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7955  -11.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6964  -10.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732   -9.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483   -9.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256   -9.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2045   -9.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -9.9914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2204  -10.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482  -10.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735  -10.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5688  -10.7174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -9.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594   -8.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -7.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2814   -7.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -8.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -9.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5155   -8.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  7 10  1  0
  2  3  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
  1 11  1  0
 20 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
 24 25  1  0
 25 26  1  0
  6  1  1  0
 11 13  1  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 14 15  1  0
 28 31  1  0
  3  4  2  0
 31 32  2  0
 15 16  1  0
 31 33  1  0
  7  8  1  0
 33 34  2  0
 15 17  2  0
 34 35  1  0
 35 36  2  0
 18 16  1  6
 36 37  1  0
 18 19  1  0
 37 38  2  0
 38 33  1  0
  7  9  1  0
 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090548

   (R)-N-(2-(1-(2-(1-(3-methylbenzoyl)piperidin-4-yl)ethyl)pyrrolidin-3-ylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide

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: 544.62

Molecular Weight (Monoisotopic): 544.2661

AlogP: 3.88

#Rotatable Bonds: 8

Polar Surface Area: 81.75

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.01

CX LogP: 3.24

CX LogD: 1.62

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.53

Np Likeness Score: -1.85

References

1. Lim JW, Oh Y, Kim JH, Oak MH, Na Y, Lee JO, Lee SW, Cho H, Park WK, Choi G, Kang J..  (2010)  Synthesis and biological evaluation of 3-aminopyrrolidine derivatives as CC chemokine receptor 2 antagonists.,  20  (7): [PMID:20223662] [10.1016/j.bmcl.2010.02.072]

Source

Source(1):

• Scientific Literature