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

ID: ALA4215630

PubChem CID: 145971359

Max Phase: Preclinical

Molecular Formula: C32H38O5

Molecular Weight: 502.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOCOc1ccc(-c2ccc(C(=O)O)cc2C)cc1-c1ccc2c(c1)C(C)(C)CCC2(C)C

Standard InChI:  InChI=1S/C32H38O5/c1-21-17-24(30(33)34)7-10-25(21)22-9-12-29(37-20-36-16-15-35-6)26(18-22)23-8-11-27-28(19-23)32(4,5)14-13-31(27,2)3/h7-12,17-19H,13-16,20H2,1-6H3,(H,33,34)

Standard InChI Key:  IFUOBHMVWSKKKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   15.9889  -17.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844  -16.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1754  -17.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1717  -14.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844  -14.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9928  -14.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8828  -15.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8828  -16.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2933  -15.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2917  -16.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9960  -16.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7023  -16.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6999  -15.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9951  -14.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4034  -14.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1127  -15.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8186  -14.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8164  -14.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1024  -13.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3994  -14.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5233  -15.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5242  -16.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2322  -16.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9397  -16.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9349  -15.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2263  -14.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6893  -13.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6844  -12.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9743  -12.5439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9694  -11.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2593  -11.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2545  -10.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5443  -10.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6515  -16.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6548  -17.4244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3575  -16.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2219  -14.1591    0.0000 C   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
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 15  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 17 21  1  0
 20 27  1  0
 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
 26 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215630

   ---

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: 502.65

Molecular Weight (Monoisotopic): 502.2719

AlogP: 7.38

#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: 4.08

CX Basic pKa: ┄

CX LogP: 7.92

CX LogD: 4.81

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.24

Np Likeness Score: 0.05

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