6-((4-Trifluromethoxyphenyl)thio)-5-methylthieno[2,3-d]pyrimidine-2,4-diamine

ID: ALA4226262

PubChem CID: 145970614

Max Phase: Preclinical

Molecular Formula: C14H12F3N5OS

Molecular Weight: 355.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc(OC(F)(F)F)cc2)[nH]c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C14H12F3N5OS/c1-6-9-10(18)20-13(19)22-11(9)21-12(6)24-8-4-2-7(3-5-8)23-14(15,16)17/h2-5H,1H3,(H5,18,19,20,21,22)

Standard InChI Key:  KOFFBPXXZBGMEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.0527  -22.0724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516  -22.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596  -23.3009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578  -21.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436  -23.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7554  -20.8463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665  -22.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4713  -22.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2513  -23.1358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7286  -22.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2435  -21.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4915  -21.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5458  -22.4659    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9586  -23.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5516  -23.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9637  -24.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7818  -24.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1860  -23.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716  -23.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1955  -25.2852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7920  -25.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2057  -26.7006    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9748  -26.0017    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.3754  -26.6990    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
 17 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4226262

   ---

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: 355.35

Molecular Weight (Monoisotopic): 355.0715

AlogP: 3.48

#Rotatable Bonds: 3

Polar Surface Area: 102.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.36

CX Basic pKa: 8.36

CX LogP: 4.35

CX LogD: 3.38

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.97

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