1-(4-Acetyl-phenyl)-3-(4-{[2-(3-methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-methyl-amino}-phenyl)-urea

ID: ALA189862

Chembl Id: CHEMBL189862

PubChem CID: 5329827

Max Phase: Preclinical

Molecular Formula: C28H28N6O4S

Molecular Weight: 544.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: TCMDC-138736 | TCMDC-138736 | TCMDC-138736|urea deriv. 21|BDBM5830|CHEMBL189862|SCHEMBL13980562|1-(4-acetylphenyl)-3-{4-[(2-{[3-(methanesulfonylmethyl)phenyl]amino}pyrimidin-4-yl)(methyl)amino]phenyl}urea

Canonical SMILES:  CC(=O)c1ccc(NC(=O)Nc2ccc(N(C)c3ccnc(Nc4cccc(CS(C)(=O)=O)c4)n3)cc2)cc1

Standard InChI:  InChI=1S/C28H28N6O4S/c1-19(35)21-7-9-22(10-8-21)31-28(36)32-23-11-13-25(14-12-23)34(2)26-15-16-29-27(33-26)30-24-6-4-5-20(17-24)18-39(3,37)38/h4-17H,18H2,1-3H3,(H,29,30,33)(H2,31,32,36)

Standard InChI Key:  GJRXTJDKSVWHHF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA189862

   Urea deriv. 21

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: 544.64

Molecular Weight (Monoisotopic): 544.1893

AlogP: 5.38

#Rotatable Bonds: 9

Polar Surface Area: 133.39

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.43

CX Basic pKa: 4.48

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.24

Np Likeness Score: -1.40

References

1. Sammond DM, Nailor KE, Veal JM, Nolte RT, Wang L, Knick VB, Rudolph SK, Truesdale AT, Nartey EN, Stafford JA, Kumar R, Cheung M..  (2005)  Discovery of a novel and potent series of dianilinopyrimidineurea and urea isostere inhibitors of VEGFR2 tyrosine kinase.,  15  (15): [PMID:15990302] [10.1016/j.bmcl.2005.05.096]

2. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

3. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

4. PubChem BioAssay data set, 

5. Toviwek B, Phuangsawai O, Konsue A, Hannongbua S, Riley J, Mutter N, Anderson M, Webster L, Hallyburton I, Read KD, Gleeson MP..  (2021)  Preparation, biological & cheminformatics-based assessment of N²,N⁴-diphenylpyrimidine-2,4-diamine as potential Kinase-targeted antimalarials.,  46  [PMID:34479064] [10.1016/j.bmc.2021.116348]

6. Toviwek B, Riley J, Mutter N, Anderson M, Webster L, Hallyburton I, Gleeson D, Read KD, Gleeson MP..  (2022)  Preparation, biological evaluation and QSAR analysis of urea substituted 2,4-diamino-pyrimidine anti-malarials.,  13  (12.0): [PMID:36561069] [10.1039/d2md00218c]

Source

Source(4):

• Scientific Literature
• GSK Malaria Screening
• PubChem BioAssays
• St Jude Leishmania Screening