2-(4'-(ethylsulfonyl)-2'-methyl-5-(trifluoromethyl)biphenyl-2-yloxy)acetic acid

ID: ALA1778639

PubChem CID: 53359023

Max Phase: Preclinical

Molecular Formula: C18H17F3O5S

Molecular Weight: 402.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)ccc2OCC(=O)O)c(C)c1

Standard InChI:  InChI=1S/C18H17F3O5S/c1-3-27(24,25)13-5-6-14(11(2)8-13)15-9-12(18(19,20)21)4-7-16(15)26-10-17(22)23/h4-9H,3,10H2,1-2H3,(H,22,23)

Standard InChI Key:  KDOSMMYSHYZFQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.0460  -11.3892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7306  -13.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7318  -14.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169  -15.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8772  -13.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3028  -16.2529    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7317  -16.2525    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0250  -16.6625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615  -12.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9748  -12.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763  -14.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  7  8  1  0
 14 15  2  0
 15 10  1  0
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  9 16  1  0
  8  9  2  0
 16 17  1  0
  9  4  1  0
 17 18  1  0
  3  2  2  0
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  8 10  1  0
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  5  6  1  0
  6 21  1  0
 10 11  2  0
 21 22  1  0
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  2  1  2  0
 11 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1778639

   2-(4''-(Ethylsulfonyl)-2''-methyl-5-(trifluoromethyl)biphenyl-2-yloxy)acetic 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: 402.39

Molecular Weight (Monoisotopic): 402.0749

AlogP: 3.94

#Rotatable Bonds: 6

Polar Surface Area: 80.67

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 3.68

CX LogD: 0.33

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -1.29

References

1. Luker T, Bonnert R, Schmidt J, Sargent C, Paine SW, Thom S, Pairaudeau G, Patel A, Mohammed R, Akam E, Dougall I, Davis AM, Abbott P, Brough S, Millichip I, McInally T..  (2011)  Switching between agonists and antagonists at CRTh2 in a series of highly potent and selective biaryl phenoxyacetic acids.,  21  (12): [PMID:21592791] [10.1016/j.bmcl.2011.04.101]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data