(2S,5R)-5-(2-Chlorophenyl)-1-(2'-methoxybiphenyl-4-carbonyl)pyrrolidine-2-carboxylic acid

ID: ALA4171128

PubChem CID: 67258265

Max Phase: Preclinical

Molecular Formula: C25H22ClNO4

Molecular Weight: 435.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1ccc(C(=O)N2[C@@H](c3ccccc3Cl)CC[C@H]2C(=O)O)cc1

Standard InChI:  InChI=1S/C25H22ClNO4/c1-31-23-9-5-3-6-18(23)16-10-12-17(13-11-16)24(28)27-21(14-15-22(27)25(29)30)19-7-2-4-8-20(19)26/h2-13,21-22H,14-15H2,1H3,(H,29,30)/t21-,22+/m1/s1

Standard InChI Key:  MCVFKGHKDGYDHZ-YADHBBJMSA-N

Molfile:  

     RDKit          2D

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    5.5428   -6.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7972   -5.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1342   -5.1343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4755   -5.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -5.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7651   -4.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0558   -5.6121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004   -5.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330   -4.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8401   -3.9074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4322   -0.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6427   -0.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356   -1.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164   -2.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8100   -3.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220   -3.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2119   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9146   -5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9063   -4.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1894   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4896   -4.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2191   -6.4213    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  9 26  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4171128

   (2S,5R)-5-(2-chlorophenyl)-1-(2''-methoxy-[1,1''-biphenyl]-4-carbonyl)pyrrolidine-2-carboxylic 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: 435.91

Molecular Weight (Monoisotopic): 435.1237

AlogP: 5.45

#Rotatable Bonds: 5

Polar Surface Area: 66.84

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.70

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 1.94

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -0.46

References

1. Hansen AH, Sergeev E, Bolognini D, Sprenger RR, Ekberg JH, Ejsing CS, McKenzie CJ, Rexen Ulven E, Milligan G, Ulven T..  (2018)  Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties.,  61  (21): [PMID:30247908] [10.1021/acs.jmedchem.8b00855]

Source

Source(1):

• Scientific Literature