rac-3-fluoro-4-(2-hydroxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetamido)benzoic acid

ID: ALA4216904

Cas Number: 185629-22-5

PubChem CID: 2418

Product Number: B287305, Order Now?

Max Phase: Preclinical

Molecular Formula: C23H26FNO4

Molecular Weight: 399.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCC(C)(C)c2cc(C(O)C(=O)Nc3ccc(C(=O)O)cc3F)ccc21

Standard InChI:  InChI=1S/C23H26FNO4/c1-22(2)9-10-23(3,4)16-11-13(5-7-15(16)22)19(26)20(27)25-18-8-6-14(21(28)29)12-17(18)24/h5-8,11-12,19,26H,9-10H2,1-4H3,(H,25,27)(H,28,29)

Standard InChI Key:  AANFHDFOMFRLLR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.2246  -23.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8158  -22.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4026  -23.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3988  -19.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8158  -20.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285  -19.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069  -21.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069  -21.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5321  -21.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5305  -21.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2422  -22.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9559  -21.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9534  -21.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2413  -20.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6672  -20.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3836  -21.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6646  -19.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0974  -20.6919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8138  -21.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8118  -21.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5274  -22.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2422  -21.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2368  -21.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5207  -20.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9615  -22.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9652  -23.1593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6747  -21.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3862  -21.9327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5146  -19.8616    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  7  5  1  0
  8  2  1  0
  2 10  1  0
  9  5  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 25 26  1  0
 25 27  2  0
 22 25  1  0
 16 28  2  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4216904

   BMS 961

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: 399.46

Molecular Weight (Monoisotopic): 399.1846

AlogP: 4.55

#Rotatable Bonds: 4

Polar Surface Area: 86.63

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: 4.76

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -0.35

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