2-(4-(4-acetamido-3-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid

ID: ALA4764051

PubChem CID: 155286423

Max Phase: Preclinical

Molecular Formula: C22H27NO4

Molecular Weight: 369.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(Cc2c(C)cc(OCC(=O)O)cc2C)cc1C(C)C

Standard InChI:  InChI=1S/C22H27NO4/c1-13(2)19-10-17(6-7-21(19)23-16(5)24)11-20-14(3)8-18(9-15(20)4)27-12-22(25)26/h6-10,13H,11-12H2,1-5H3,(H,23,24)(H,25,26)

Standard InChI Key:  GZHDROJXCQEXMK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    4.0226   -3.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -4.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295   -4.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392   -4.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4364   -3.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277   -3.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -3.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3146   -2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -3.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -4.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -5.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -6.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202   -6.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1425   -3.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8518   -3.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8515   -4.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5599   -4.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2671   -4.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2613   -3.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5524   -3.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9769   -4.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6825   -4.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3922   -4.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3990   -5.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1005   -4.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444   -4.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5451   -2.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  7  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  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
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 16 26  1  0
 20 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764051

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 369.46

Molecular Weight (Monoisotopic): 369.1940

AlogP: 4.44

#Rotatable Bonds: 7

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.91

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 1.69

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.47

References

1. Runfola M,Sestito S,Bellusci L,La Pietra V,D'Amore VM,Kowalik MA,Chiellini G,Gul S,Perra A,Columbano A,Marinelli L,Novellino E,Rapposelli S.  (2020)  Design, synthesis and biological evaluation of novel TRβ selective agonists sustained by ADME-toxicity analysis.,  188  [PMID:31931337] [10.1016/j.ejmech.2019.112006]

Source

Source(1):

• Scientific Literature