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

ID: ALA4210595

PubChem CID: 16661644

Max Phase: Preclinical

Molecular Formula: C30H34O4

Molecular Weight: 458.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCC(C)(C)c2cc(-c3cc(-c4ccc(C(=O)O)cc4)ccc3OCCCO)ccc21

Standard InChI:  InChI=1S/C30H34O4/c1-29(2)14-15-30(3,4)26-19-23(10-12-25(26)29)24-18-22(11-13-27(24)34-17-5-16-31)20-6-8-21(9-7-20)28(32)33/h6-13,18-19,31H,5,14-17H2,1-4H3,(H,32,33)

Standard InChI Key:  CPUYTQLSRRIINE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.3924   -3.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.8079   -3.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8031   -2.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0945   -2.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5197   -3.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5230   -4.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2257   -3.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5575   -0.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5526   -0.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8425    0.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8377    1.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1275    1.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 17 21  1  0
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 27 29  2  0
 24 27  1  0
 20 30  1  0
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 31 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4210595

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

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: 458.60

Molecular Weight (Monoisotopic): 458.2457

AlogP: 6.83

#Rotatable Bonds: 7

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.08

CX Basic pKa: ┄

CX LogP: 6.76

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: 0.31

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