(S)-Methyl 4-methyl-3-(2-((3-(trifluoromethoxy)phenyl)-carbamoyl)-Pyrrolidine-1-carboxamido)Benzoate

ID: ALA4093577

PubChem CID: 137654246

Max Phase: Preclinical

Molecular Formula: C22H22F3N3O5

Molecular Weight: 465.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(C)c(NC(=O)N2CCC[C@H]2C(=O)Nc2cccc(OC(F)(F)F)c2)c1

Standard InChI:  InChI=1S/C22H22F3N3O5/c1-13-8-9-14(20(30)32-2)11-17(13)27-21(31)28-10-4-7-18(28)19(29)26-15-5-3-6-16(12-15)33-22(23,24)25/h3,5-6,8-9,11-12,18H,4,7,10H2,1-2H3,(H,26,29)(H,27,31)/t18-/m0/s1

Standard InChI Key:  OXJNFQCZBTXOSU-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   18.1722   -8.7085    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.4664   -8.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4655   -9.1154    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7361   -7.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0305   -7.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3220   -7.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6123   -7.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6111   -8.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9056   -9.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9044  -10.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1971   -8.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1983   -7.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3196   -9.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0293   -8.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3232   -6.7465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0329   -6.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7373   -6.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0300   -5.5217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6939   -5.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4404   -4.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6232   -4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3715   -5.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4708   -5.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6828   -6.0819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4699   -6.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6819   -7.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4689   -7.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0481   -6.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8361   -5.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0491   -5.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6809   -8.0859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0500   -4.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0482   -7.7247    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  8 13  1  0
 13 14  2  0
  5 14  1  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
 19 23  1  1
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 25 30  1  0
 27 31  1  0
 31  2  1  0
 23 32  2  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093577

   ---

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: 465.43

Molecular Weight (Monoisotopic): 465.1512

AlogP: 4.32

#Rotatable Bonds: 5

Polar Surface Area: 96.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.71

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.80

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.64

Np Likeness Score: -1.79

References

1. Vulpetti A, Randl S, Rüdisser S, Ostermann N, Erbel P, Mac Sweeney A, Zoller T, Salem B, Gerhartz B, Cumin F, Hommel U, Dalvit C, Lorthiois E, Maibaum J..  (2017)  Structure-Based Library Design and Fragment Screening for the Identification of Reversible Complement Factor D Protease Inhibitors.,  60  (5): [PMID:28157311] [10.1021/acs.jmedchem.6b01684]

Source

Source(1):

• Scientific Literature