(3-{4-[5-[(3,4-Dimethoxy-phenyl)-methylamino]-1-(4-fluoro-phenyl)-1H-imidazol-2-ylsulfanylmethyl]-3,5-difluoro-phenyl}-prop-2-ynyl)-trimethylammonium iodide

ID: ALA4086463

PubChem CID: 118577308

Max Phase: Preclinical

Molecular Formula: C31H32F3IN4O2S

Molecular Weight: 581.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N(C)c2cnc(SCc3c(F)cc(C#CC[N+](C)(C)C)cc3F)n2-c2ccc(F)cc2)cc1OC.[I-]

Standard InChI:  InChI=1S/C31H32F3N4O2S.HI/c1-36(24-13-14-28(39-5)29(18-24)40-6)30-19-35-31(37(30)23-11-9-22(32)10-12-23)41-20-25-26(33)16-21(17-27(25)34)8-7-15-38(2,3)4;/h9-14,16-19H,15,20H2,1-6H3;1H/q+1;/p-1

Standard InChI Key:  NIERUOACYBGPDK-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

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    9.6528   -4.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3306   -4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3881   -3.5968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5579   -4.6566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9412   -4.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4017   -5.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0993   -3.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1725   -4.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7846   -4.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6313   -4.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -2.5158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252   -2.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  6  1  0
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  7  8  2  0
  8  9  1  0
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 10 11  1  0
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  6 10  1  0
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 19 24  2  0
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 20 26  1  0
 27 28  3  0
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  3 30  1  0
 29  3  1  0
 22 27  1  0
  5 17  1  0
  7 31  1  0
 31 32  1  0
 31 33  1  0
 32 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 32  1  0
 39 40  1  0
 37 39  1  0
 41 42  1  0
 36 41  1  0
M  CHG  2   1  -1   3   1
M  END

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: 581.68

Molecular Weight (Monoisotopic): 581.2193

AlogP: 6.42

#Rotatable Bonds: 9

Polar Surface Area: 39.52

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 5.15

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.13

Np Likeness Score: -1.12

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