3'-chloro-4'-((2-methoxyethoxy)methoxy)-5'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)biphenyl-4-carboxylic acid

ID: ALA4214493

PubChem CID: 145973883

Max Phase: Preclinical

Molecular Formula: C31H35ClO5

Molecular Weight: 523.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOCOc1c(Cl)cc(-c2ccc(C(=O)O)cc2)cc1-c1ccc2c(c1)C(C)(C)CCC2(C)C

Standard InChI:  InChI=1S/C31H35ClO5/c1-30(2)12-13-31(3,4)26-17-22(10-11-25(26)30)24-16-23(20-6-8-21(9-7-20)29(33)34)18-27(32)28(24)37-19-36-15-14-35-5/h6-11,16-18H,12-15,19H2,1-5H3,(H,33,34)

Standard InChI Key:  SLNCTKGASCOEAI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.2069  -14.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7979  -15.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941  -12.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069  -13.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8488  -13.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117  -11.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069  -11.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5967  -10.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8818   -9.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -8.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668   -8.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2739  -14.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2772  -15.5424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9800  -14.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194  -11.0581    0.0000 Cl  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
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  2 10  1  0
  9  5  1  0
  9 10  2  0
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 17 21  1  0
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 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 34 35  1  0
 34 36  2  0
 24 34  1  0
 19 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4214493

   ---

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: 523.07

Molecular Weight (Monoisotopic): 522.2173

AlogP: 7.72

#Rotatable Bonds: 9

Polar Surface Area: 64.99

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 8.01

CX LogD: 4.90

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.23

Np Likeness Score: 0.10

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