6-((4,4-dimethylthiochroman-6-yl)ethynyl)picolinic acid

ID: ALA4212472

PubChem CID: 145965542

Max Phase: Preclinical

Molecular Formula: C19H17NO2S

Molecular Weight: 323.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCSc2ccc(C#Cc3cccc(C(=O)O)n3)cc21

Standard InChI:  InChI=1S/C19H17NO2S/c1-19(2)10-11-23-17-9-7-13(12-15(17)19)6-8-14-4-3-5-16(20-14)18(21)22/h3-5,7,9,12H,10-11H2,1-2H3,(H,21,22)

Standard InChI Key:  GTCFCUSLARKKEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.5076   -9.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0988   -8.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856   -9.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5291   -8.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463   -8.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -7.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273   -7.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136   -8.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177   -7.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104   -7.0069    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945   -7.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -8.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620   -8.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6731   -9.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3876   -9.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3821  -10.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0957  -10.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8125  -10.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8113   -9.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0972   -9.0688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5273   -9.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2432   -9.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5258   -8.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  8  2  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  2  1  0
  5 13  1  0
 13 14  3  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  1  0
 21 23  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4212472

   ---

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: 323.42

Molecular Weight (Monoisotopic): 323.0980

AlogP: 3.95

#Rotatable Bonds: 1

Polar Surface Area: 50.19

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.94

CX Basic pKa: 5.42

CX LogP: 3.27

CX LogD: 1.63

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: -0.45

References

1. Thoreau E, Arlabosse JM, Bouix-Peter C, Chambon S, Chantalat L, Daver S, Dumais L, Duvert G, Feret A, Ouvry G, Pascau J, Raffin C, Rodeville N, Soulet C, Tabet S, Talano S, Portal T..  (2018)  Structure-based design of Trifarotene (CD5789), a potent and selective RARγ agonist for the treatment of acne.,  28  (10): [PMID:29706423] [10.1016/j.bmcl.2018.04.036]

Source

Source(1):

• Scientific Literature