2-(Biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid

ID: ALA348270

PubChem CID: 9948506

Max Phase: Preclinical

Molecular Formula: C19H17NO3

Molecular Weight: 307.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1=C(C(=O)Nc2ccc(-c3ccccc3)cc2)CCC1

Standard InChI:  InChI=1S/C19H17NO3/c21-18(16-7-4-8-17(16)19(22)23)20-15-11-9-14(10-12-15)13-5-2-1-3-6-13/h1-3,5-6,9-12H,4,7-8H2,(H,20,21)(H,22,23)

Standard InChI Key:  KKMNLDWJDASMGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.4000    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125    1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -0.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250    1.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792    2.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3417   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5625   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  2  2  0
  7 11  2  0
  8  4  2  0
  9  5  1  0
 10  7  1  0
 11 17  1  0
 12 16  2  0
 13  4  1  0
 14  1  1  0
 15  3  1  0
 16  9  1  0
 17  9  2  0
 18 14  1  0
 19 10  1  0
 20 10  2  0
 21 20  1  0
 22 19  2  0
 23 21  2  0
 18 15  1  0
 12  7  1  0
 23 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA348270

   2-[(4-Phenylphenyl)carbamoyl]cyclopent-1-ene-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: 307.35

Molecular Weight (Monoisotopic): 307.1208

AlogP: 3.86

#Rotatable Bonds: 4

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.31

CX Basic pKa: ┄

CX LogP: 3.81

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.90

Np Likeness Score: -0.50

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. Leban J, Kralik M, Mies J, Baumgartner R, Gassen M, Tasler S..  (2006)  Biphenyl-4-ylcarbamoyl thiophene carboxylic acids as potent DHODH inhibitors.,  16  (2): [PMID:16246558] [10.1016/j.bmcl.2005.10.011]

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