5,7-dimethyl-6-((4-(trifluoromethoxy)phenyl)thio)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4225860

PubChem CID: 145968315

Max Phase: Preclinical

Molecular Formula: C15H14F3N5OS

Molecular Weight: 369.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc(OC(F)(F)F)cc2)n(C)c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C15H14F3N5OS/c1-7-10-11(19)21-14(20)22-12(10)23(2)13(7)25-9-5-3-8(4-6-9)24-15(16,17)18/h3-6H,1-2H3,(H4,19,20,21,22)

Standard InChI Key:  WYEYSYWLOCOUSM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.8726  -27.9124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8715  -28.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5795  -29.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5777  -27.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1634  -29.1400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5753  -26.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2864  -27.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2911  -28.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0712  -28.9759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5485  -28.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0634  -27.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3114  -26.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3657  -28.3059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7785  -29.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3715  -29.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7836  -30.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6017  -30.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0059  -29.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5915  -29.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3282  -29.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0153  -31.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8325  -31.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2462  -31.8241    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.2360  -30.4087    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.6468  -31.1193    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  2  5  1  0
  4  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  9 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4225860

   ---

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: 369.37

Molecular Weight (Monoisotopic): 369.0871

AlogP: 3.49

#Rotatable Bonds: 3

Polar Surface Area: 91.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.95

CX LogP: 4.58

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -1.14

References

1. Shah K, Lin X, Queener SF, Cody V, Pace J, Gangjee A..  (2018)  Targeting species specific amino acid residues: Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors and potential anti-opportunistic infection agents.,  26  (9): [PMID:29691153] [10.1016/j.bmc.2018.04.032]

Source

Source(1):

• Scientific Literature