2-(2,3,5,6-Tetrafluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid

ID: ALA154623

PubChem CID: 10457096

Max Phase: Preclinical

Molecular Formula: C20H12F7NO4

Molecular Weight: 463.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1=C(C(=O)Nc2c(F)c(F)c(-c3cccc(OC(F)(F)F)c3)c(F)c2F)CCC1

Standard InChI:  InChI=1S/C20H12F7NO4/c21-13-12(8-3-1-4-9(7-8)32-20(25,26)27)14(22)16(24)17(15(13)23)28-18(29)10-5-2-6-11(10)19(30)31/h1,3-4,7H,2,5-6H2,(H,28,29)(H,30,31)

Standard InChI Key:  HXVDQTDBVMYWOO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.1500   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250   -0.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792    0.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250    0.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708    1.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042    0.8833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -1.9750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -1.9792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    0.0583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    1.7083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292    0.8833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    2.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  2  0
  4  1  1  0
  5  4  2  0
  6  3  1  0
  7  1  1  0
  8  7  1  0
  9  8  1  0
 10  9  2  0
 11  2  1  0
 12 15  1  0
 13 10  1  0
 14 11  1  0
 15 18  1  0
 16  8  2  0
 17 13  2  0
 18 14  2  0
 19  5  1  0
 20  6  1  0
 21  4  1  0
 22  3  1  0
 23 12  1  0
 24 12  1  0
 25 12  1  0
 26 13  1  0
 27  9  1  0
 28 10  1  0
 29 11  2  0
 30 27  1  0
 31 29  1  0
 32 31  2  0
  2  6  2  0
 30 28  1  0
 18 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA154623

   2-[[2,3,5,6-Tetrafluoro-4-[3-(trifluoromethoxy)phenyl]phenyl]carbamoyl]cyclopentene-1-carboxylic acid

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: 463.31

Molecular Weight (Monoisotopic): 463.0655

AlogP: 5.31

#Rotatable Bonds: 5

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.44

CX Basic pKa: ┄

CX LogP: 5.81

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -0.59

References

1. Leban J, Saeb W, Garcia G, Baumgartner R, Kramer B..  (2004)  Discovery of a novel series of DHODH inhibitors by a docking procedure and QSAR refinement.,  14  (1): [PMID:14684297] [10.1016/j.bmcl.2003.10.021]

2. Leban J, Kralik M, Mies J, Gassen M, Tentschert K, Baumgartner R..  (2005)  SAR, species specificity, and cellular activity of cyclopentene dicarboxylic acid amides as DHODH inhibitors.,  15  (21): [PMID:16143532] [10.1016/j.bmcl.2005.07.053]

3. Baumgartner R, Walloschek M, Kralik M, Gotschlich A, Tasler S, Mies J, Leban J..  (2006)  Dual binding mode of a novel series of DHODH inhibitors.,  49  (4): [PMID:16480261] [10.1021/jm0506975]

4. Mancini RS, Barden CJ, Weaver DF, Reed MA..  (2021)  Furazans in Medicinal Chemistry.,  64  (4.0): [PMID:33569941] [10.1021/acs.jmedchem.0c01901]

Source

Source(1):

• Scientific Literature