4-([2,4-Di-tert-butyl]phenoxymethyl)benzoic acid

ID: ALA4560581

PubChem CID: 14850625

Max Phase: Preclinical

Molecular Formula: C22H28O3

Molecular Weight: 340.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(OCc2ccc(C(=O)O)cc2)c(C(C)(C)C)c1

Standard InChI:  InChI=1S/C22H28O3/c1-21(2,3)17-11-12-19(18(13-17)22(4,5)6)25-14-15-7-9-16(10-8-15)20(23)24/h7-13H,14H2,1-6H3,(H,23,24)

Standard InChI Key:  PFUVKFKOVKCVAJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    5.9624  -14.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9613  -15.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6693  -15.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3790  -15.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3762  -14.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6675  -14.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0884  -15.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0897  -16.4560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7955  -15.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2546  -14.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470  -14.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392  -14.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8426  -13.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357  -12.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271  -13.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299  -14.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375  -14.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5512  -12.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581  -13.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5530  -11.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -12.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187  -12.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7174  -11.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117  -13.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0070  -12.3693    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
  7  8  1  0
  7  9  2  0
  4  7  1  0
  1 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 13 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560581

   4-[(2,4-Ditert-butylphenoxy)methyl]benzoic acid

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: 340.46

Molecular Weight (Monoisotopic): 340.2038

AlogP: 5.56

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 6.29

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: -0.55

References

1. Heitel P, Gellrich L, Kalinowsky L, Heering J, Kaiser A, Ohrndorf J, Proschak E, Merk D..  (2019)  Computer-Assisted Discovery and Structural Optimization of a Novel Retinoid X Receptor Agonist Chemotype.,  10  (2): [PMID:30783504] [10.1021/acsmedchemlett.8b00551]

2. Zhang, L L and 7 more authors.  1996-07-05  Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells.  [PMID:8709094]

3. Canan Koch, S S SS and 6 more authors.  1999-02-25  Synthesis of retinoid X receptor-specific ligands that are potent inducers of adipogenesis in 3T3-L1 cells.  [PMID:10052980]

Source

Source(1):

• Scientific Literature