3-[2-[(2,6-Difluorophenyl)methylsulfanyl]-5-(3,4-dimethoxy-N-methyl-anilino)-1-(4-fluorophenyl)imidazol-4-yl]propanoic Acid

ID: ALA4090586

PubChem CID: 126700763

Max Phase: Preclinical

Molecular Formula: C28H26F3N3O4S

Molecular Weight: 557.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N(C)c2c(CCC(=O)O)nc(SCc3c(F)cccc3F)n2-c2ccc(F)cc2)cc1OC

Standard InChI:  InChI=1S/C28H26F3N3O4S/c1-33(19-11-13-24(37-2)25(15-19)38-3)27-23(12-14-26(35)36)32-28(34(27)18-9-7-17(29)8-10-18)39-16-20-21(30)5-4-6-22(20)31/h4-11,13,15H,12,14,16H2,1-3H3,(H,35,36)

Standard InChI Key:  NLFAQCWDVWTFLW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.1408   -5.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8501   -6.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1922   -6.6870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5277   -6.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7737   -5.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5909   -5.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2904   -4.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1971   -7.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9066   -7.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.2161   -9.9556    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.6259   -6.4496    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4353   -4.7983    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.3107   -5.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9196   -4.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7554   -5.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3685   -6.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9820   -5.9024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8195   -6.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3102   -4.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5348   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5892   -7.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6188   -4.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1350   -3.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4634   -2.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3227   -3.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
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  5  6  2  0
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  3  7  2  0
  6  8  1  0
  9 10  1  0
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  9 14  2  0
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  4  9  1  0
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 18 23  2  0
 16 17  1  0
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 19 25  1  0
  3 16  1  0
  1  5  1  0
  2 26  2  0
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 27 28  2  0
 28 29  1  0
 29 30  2  0
 30  2  1  0
 31 32  1  0
 29 31  1  0
 33 34  1  0
 28 33  1  0
  1 35  1  0
  8 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090586

   ---

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: 557.59

Molecular Weight (Monoisotopic): 557.1596

AlogP: 6.38

#Rotatable Bonds: 11

Polar Surface Area: 76.82

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.48

CX Basic pKa: 4.82

CX LogP: 5.20

CX LogD: 3.16

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.21

Np Likeness Score: -1.24

References

1. Lasalle M, Hoguet V, Hennuyer N, Leroux F, Piveteau C, Belloy L, Lestavel S, Vallez E, Dorchies E, Duplan I, Sevin E, Culot M, Gosselet F, Boulahjar R, Herledan A, Staels B, Deprez B, Tailleux A, Charton J..  (2017)  Topical Intestinal Aminoimidazole Agonists of G-Protein-Coupled Bile Acid Receptor 1 Promote Glucagon Like Peptide-1 Secretion and Improve Glucose Tolerance.,  60  (10): [PMID:28414465] [10.1021/acs.jmedchem.6b01873]

Source

Source(1):

• Scientific Literature