6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methyl-quinoline-4-carbohydroxamic acid

ID: ALA4759615

PubChem CID: 162657691

Max Phase: Preclinical

Molecular Formula: C23H16F2N2O2

Molecular Weight: 390.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(-c2ccc(-c3ccccc3F)cc2)nc2ccc(F)cc2c1C(=O)NO

Standard InChI:  InChI=1S/C23H16F2N2O2/c1-13-21(23(28)27-29)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12,29H,1H3,(H,27,28)

Standard InChI Key:  GAYOEHUUOCPGQU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.4449   -5.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529   -5.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -4.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8598   -4.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -5.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -5.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2773   -5.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726   -4.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5635   -4.1467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866   -5.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -4.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6889   -4.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3936   -4.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3891   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6739   -2.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9721   -3.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917   -2.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8027   -3.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5069   -2.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5012   -2.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7855   -1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0843   -2.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3725   -1.6884    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369   -5.7881    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5708   -6.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8639   -7.0103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2793   -7.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -7.8275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
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 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
 23 24  1  0
  2 25  1  0
  7 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759615

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.39

Molecular Weight (Monoisotopic): 390.1180

AlogP: 5.27

#Rotatable Bonds: 3

Polar Surface Area: 62.22

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.90

CX Basic pKa: 1.28

CX LogP: 5.46

CX LogD: 5.44

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -1.03

References

1. DeRatt LG,Christine Pietsch E,Tanner A,Shaffer P,Jacoby E,Wang W,Kazmi F,Zhang X,Attar RM,Edwards JP,Kuduk SD.  (2020)  A carboxylic acid isostere screen of the DHODH inhibitor Brequinar.,  30  (22): [PMID:33007394] [10.1016/j.bmcl.2020.127589]

Source

Source(1):

• Scientific Literature