US8759366, (1S,4R)-4-hydroxy-2,2-dimethyl-4-(5-{3-methyl-5-[(4-methylpyrimidin-2-yl)-amino]phenyl}-1,3-thiazol-2-yl)cyclohexanecarboxylic acid

ID: ALA3685796

Chembl Id: CHEMBL3685796

Cas Number: 1312534-69-2

PubChem CID: 53251189

Max Phase: Preclinical

Molecular Formula: C24H28N4O3S

Molecular Weight: 452.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2nccc(C)n2)cc(-c2cnc([C@@]3(O)CC[C@H](C(=O)O)C(C)(C)C3)s2)c1

Standard InChI:  InChI=1S/C24H28N4O3S/c1-14-9-16(11-17(10-14)28-22-25-8-6-15(2)27-22)19-12-26-21(32-19)24(31)7-5-18(20(29)30)23(3,4)13-24/h6,8-12,18,31H,5,7,13H2,1-4H3,(H,29,30)(H,25,27,28)/t18-,24-/m1/s1

Standard InChI Key:  OYKPWSZSBLRRPL-HOYKHHGWSA-N

Alternative Forms

1. Parent:

   

   ALA3685796

   MRL-SYKi

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

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: 452.58

Molecular Weight (Monoisotopic): 452.1882

AlogP: 5.06

#Rotatable Bonds: 5

Polar Surface Area: 108.23

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.59

CX Basic pKa: 2.55

CX LogP: 4.26

CX LogD: 1.52

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.45

References

1.  (2014)  Aminopyrimidines as SYK inhibitors, 

2. SGC Frankfurt.  (2021)  Data for DCP probe MRL-SYKi,  [10.6019/CHEMBL4507285]

3.  (2021)  EUbOPEN Chemogenomics Library wave 1,  [10.6019/CHEMBL4689842]

4. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

5. EUbOPEN.  (2023)  Affinity Phenotypic Cellular Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5209897]

6. EUbOPEN.  (2023)  Affinity Biochemical Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5210307]

7. EUbOPEN.  (2023)  Selectivity Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5212743]

Source

Source(4):

• BindingDB Database
• Donated Chemical Probes - SGC Frankfurt
• EUbOPEN Chemogenomic Library
• Literature data from EUbOPEN Chemogenomic Library