(R)-(4-cyclopropyl-3,4-dihydroquinoxaline-1(2H)-yl)(3-(2,5-dichlorobenzyl)thiazolidin-4-yl)methanone

ID: ALA4205214

PubChem CID: 71660821

Max Phase: Preclinical

Molecular Formula: C22H23Cl2N3OS

Molecular Weight: 448.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([C@@H]1CSCN1Cc1cc(Cl)ccc1Cl)N1CCN(C2CC2)c2ccccc21

Standard InChI:  InChI=1S/C22H23Cl2N3OS/c23-16-5-8-18(24)15(11-16)12-25-14-29-13-21(25)22(28)27-10-9-26(17-6-7-17)19-3-1-2-4-20(19)27/h1-5,8,11,17,21H,6-7,9-10,12-14H2/t21-/m0/s1

Standard InChI Key:  QFJZLEQGGSAPMB-NRFANRHFSA-N

Molfile:  

     RDKit          2D

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    9.1397  -16.0680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5804  -15.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7817  -15.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9002  -16.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1086  -17.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8735  -17.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4291  -18.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2229  -18.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5319  -15.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0280  -17.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0268  -18.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349  -19.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4445  -18.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417  -17.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331  -17.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7306  -16.6035    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7347  -19.8753    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1479  -17.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8571  -17.8207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9497  -18.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7497  -18.8034    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1557  -18.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065  -17.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7757  -16.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679  -16.1432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  1  4  1  0
  5  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  2  0
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  7  8  2  0
  8  9  1  0
  9 10  2  0
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 11 13  1  0
  2 11  1  0
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 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 19 20  1  0
 16 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 27 28  1  6
 28  1  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4205214

   (4-cyclopropyl-2,3-dihydroquinoxalin-1-yl)-[(4R)-3-[(2,5-dichlorophenyl)methyl]-1,3-thiazolidin-4-yl]methanone

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: 448.42

Molecular Weight (Monoisotopic): 447.0939

AlogP: 4.88

#Rotatable Bonds: 4

Polar Surface Area: 26.79

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.64

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.48

References

1. Chen T, Reich NW, Bell N, Finn PD, Rodriguez D, Kohler J, Kozuka K, He L, Spencer AG, Charmot D, Navre M, Carreras CW, Koo-McCoy S, Tabora J, Caldwell JS, Jacobs JW, Lewis JG..  (2018)  Design of Gut-Restricted Thiazolidine Agonists of G Protein-Coupled Bile Acid Receptor 1 (GPBAR1, TGR5).,  61  (17): [PMID:30141927] [10.1021/acs.jmedchem.8b00308]

Source

Source(1):

• Scientific Literature