5-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)butoxy)-2-methylbenzoic acid

ID: ALA4875695

PubChem CID: 164627946

Max Phase: Preclinical

Molecular Formula: C25H32O6

Molecular Weight: 428.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(OCCCCOc2ccc(C(=O)CC(C)(C)C)c(O)c2C)cc1C(=O)O

Standard InChI:  InChI=1S/C25H32O6/c1-16-8-9-18(14-20(16)24(28)29)30-12-6-7-13-31-22-11-10-19(23(27)17(22)2)21(26)15-25(3,4)5/h8-11,14,27H,6-7,12-13,15H2,1-5H3,(H,28,29)

Standard InChI Key:  QNESRDXUJUOVAO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.4128   -9.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4116  -10.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1197  -11.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8294  -10.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8265   -9.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1179   -9.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7050   -9.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1155   -8.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5327   -9.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2419   -9.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5296   -8.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9481   -9.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6573   -9.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9450   -8.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6529   -9.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7036  -11.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9962  -10.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2882  -11.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5808  -10.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728  -11.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654  -10.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4574  -11.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526  -10.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0450  -11.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0440  -11.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7563  -12.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4609  -11.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379  -10.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389   -9.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6296  -11.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3365  -12.3201    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
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 24 28  1  0
 28 29  2  0
 28 30  1  0
 25 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875695

   ---

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: 428.53

Molecular Weight (Monoisotopic): 428.2199

AlogP: 5.56

#Rotatable Bonds: 10

Polar Surface Area: 93.06

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.70

CX Basic pKa: ┄

CX LogP: 6.36

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -0.23

References

1. Yamada Y, Gilliland K, Xiang Z, Haymer D, Crocker KE, Loch MT, Schulte ML, Rodriguez AL, Niswender CM, Jeffrey Conn P, Lindsley CW, Melancon BJ..  (2021)  Positive allosteric modulators (PAMs) of the group II metabotropic glutamate receptors: Design, synthesis, and evaluation as ex-vivo tool compounds.,  50  [PMID:34461178] [10.1016/j.bmcl.2021.128342]

Source

Source(1):

• Scientific Literature