2-(5-(2-(2,6-Dichloro-benzoylamino)-phenyl)-pentyl)benzoic Acid

ID: ALA5286769

Max Phase: Preclinical

Molecular Formula: C25H23Cl2NO3

Molecular Weight: 456.37

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1CCCCCc1ccccc1NC(=O)c1c(Cl)cccc1Cl

Standard InChI:  InChI=1S/C25H23Cl2NO3/c26-20-14-8-15-21(27)23(20)24(29)28-22-16-7-5-12-18(22)11-3-1-2-9-17-10-4-6-13-19(17)25(30)31/h4-8,10,12-16H,1-3,9,11H2,(H,28,29)(H,30,31)

Standard InChI Key:  WYWBHJUKDWBYGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.1354    0.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1502    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    2.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4567    2.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451    1.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7252    1.0686    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4136   -0.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579   -1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422   -1.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637   -2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499   -2.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347   -2.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344   -1.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -1.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7056   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104   -1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232   -1.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393   -1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1521   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493   -2.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658   -2.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5805   -2.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5794   -1.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676   -1.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8721   -0.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    0.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878    0.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422   -0.1973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878    1.0355    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  1  9  2  0
 10 11  2  0
 12 10  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 11 15  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 21 26  2  0
 26 25  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 11 30  1  0
  1 30  1  0
  3 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286769

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.37

Molecular Weight (Monoisotopic): 455.1055

AlogP: 6.90

#Rotatable Bonds: 9

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.91

CX Basic pKa: ┄

CX LogP: 7.80

CX LogD: 4.59

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: -0.79

References

1. Heinrich T, Sala-Hojman A, Ferretti R, Petersson C, Minguzzi S, Gondela A, Ramaswamy S, Bartosik A, Czauderna F, Crowley L, Wahra P, Schilke H, Böpple P, Dudek Ł, Leś M, Niedziejko P, Olech K, Pawlik H, Włoszczak Ł, Zuchowicz K, Suarez Alvarez JR, Martyka J, Sitek E, Mikulski M, Szczęśniak J, Jäckel S, Krier M, Król M, Wegener A, Gałęzowski M, Nowak M, Becker F, Herhaus C..  (2021)  Discovery of 5-{2-[5-Chloro-2-(5-ethoxyquinoline-8-sulfonamido)phenyl]ethynyl}-4-methoxypyridine-2-carboxylic Acid, a Highly Selective in Vivo Useable Chemical Probe to Dissect MCT4 Biology.,  64  (16.0): [PMID:34382802] [10.1021/acs.jmedchem.1c00448]

Source

Source(1):

• Scientific Literature