2-(4-chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)butanoic acid

ID: ALA4536821

PubChem CID: 11978566

Max Phase: Preclinical

Molecular Formula: C16H18ClN3O2S

Molecular Weight: 351.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(Sc1nc(Cl)cc(Nc2cccc(C)c2C)n1)C(=O)O

Standard InChI:  InChI=1S/C16H18ClN3O2S/c1-4-12(15(21)22)23-16-19-13(17)8-14(20-16)18-11-7-5-6-9(2)10(11)3/h5-8,12H,4H2,1-3H3,(H,21,22)(H,18,19,20)

Standard InChI Key:  QOGGHJNOQATQIO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   32.9462   -2.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9451   -3.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6531   -3.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3628   -3.4728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3600   -2.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6514   -2.2449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2384   -2.2453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5308   -2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8231   -2.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1160   -2.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1158   -3.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8285   -3.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5328   -3.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8239   -1.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4084   -2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0661   -2.2389    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.7754   -2.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4816   -2.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1908   -2.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4785   -1.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6529   -4.6995    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.7785   -3.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4877   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  9 14  1  0
 10 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  3 21  1  0
 17 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536821

   2-[4-Chloro-6-(2,3-dimethylanilino)pyrimidin-2-yl]sulfanylbutanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 351.86

Molecular Weight (Monoisotopic): 351.0808

AlogP: 4.45

#Rotatable Bonds: 6

Polar Surface Area: 75.11

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.78

CX Basic pKa: 2.80

CX LogP: 4.82

CX LogD: 2.08

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.45

Np Likeness Score: -1.39

References

1. Pollinger J, Gellrich L, Schierle S, Kilu W, Schmidt J, Kalinowsky L, Ohrndorf J, Kaiser A, Heering J, Proschak E, Merk D..  (2019)  Tuning Nuclear Receptor Selectivity of Wy14,643 towards Selective Retinoid X Receptor Modulation.,  62  (4): [PMID:30702885] [10.1021/acs.jmedchem.8b01848]

2. Zhang, L L and 7 more authors.  1996-07-05  Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells.  [PMID:8709094]

3. Canan Koch, S S SS and 6 more authors.  1999-02-25  Synthesis of retinoid X receptor-specific ligands that are potent inducers of adipogenesis in 3T3-L1 cells.  [PMID:10052980]

Source

Source(1):

• Scientific Literature