(S)-3-[4-(4'-Chloro-2'-methyl-biphenyl-3-ylmethoxy)-phenyl]-3-(1-methyl-1H-imidazol-2-yl)-propionic acid

ID: ALA3287569

Chembl Id: CHEMBL3287569

Cas Number: 916219-50-6

PubChem CID: 11961321

Max Phase: Preclinical

Molecular Formula: C27H25ClN2O3

Molecular Weight: 460.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Cl)ccc1-c1cccc(COc2ccc([C@H](CC(=O)O)c3nccn3C)cc2)c1

Standard InChI:  InChI=1S/C27H25ClN2O3/c1-18-14-22(28)8-11-24(18)21-5-3-4-19(15-21)17-33-23-9-6-20(7-10-23)25(16-26(31)32)27-29-12-13-30(27)2/h3-15,25H,16-17H2,1-2H3,(H,31,32)/t25-/m0/s1

Standard InChI Key:  GFFXCPIMXLSUGF-VWLOTQADSA-N

Alternative Forms

1. Parent:

   

   ALA3287569

   (S)-3-[4-(4'-Chloro-2'-methyl-biphenyl-3-ylmethoxy)-phenyl]-3-(1-methyl-1H-imidazol-2-yl)-propionic 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: 460.96

Molecular Weight (Monoisotopic): 460.1554

AlogP: 6.23

#Rotatable Bonds: 8

Polar Surface Area: 64.35

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.97

CX Basic pKa: 6.00

CX LogP: 4.78

CX LogD: 3.44

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -0.85

References

1. Liu JJ, Wang Y, Ma Z, Schmitt M, Zhu L, Brown SP, Dransfield PJ, Sun Y, Sharma R, Guo Q, Zhuang R, Zhang J, Luo J, Tonn GR, Wong S, Swaminath G, Medina JC, Lin DC, Houze JB..  (2014)  Optimization of GPR40 Agonists for Type 2 Diabetes.,  5  (5): [PMID:24900872] [10.1021/ml400501x]

2. Ma Z, Lin DC, Sharma R, Liu J, Zhu L, Li AR, Kohn T, Wang Y, Liu JJ, Bartberger MD, Medina JC, Zhuang R, Li F, Zhang J, Luo J, Wong S, Tonn GR, Houze JB..  (2016)  Discovery of the imidazole-derived GPR40 agonist AM-3189.,  26  (1): [PMID:26620255] [10.1016/j.bmcl.2015.11.050]

3. Chen T, Ning M, Ye Y, Wang K, Leng Y, Shen J..  (2018)  Design, synthesis and structure-activity relationship studies of GPR40 agonists containing amide linker.,  152  [PMID:29705709] [10.1016/j.ejmech.2018.04.023]

Source

Source(1):

• Scientific Literature