2,4-Diamino-5-methyl-6-(2',3',5',6'-tetrafluoro-4'-trifluoromethylphenylsulfanyl)-furo[2,3-d]pyrimidine

ID: ALA604722

PubChem CID: 46231410

Max Phase: Preclinical

Molecular Formula: C14H7F7N4OS

Molecular Weight: 412.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2c(F)c(F)c(C(F)(F)F)c(F)c2F)oc2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C14H7F7N4OS/c1-2-3-10(22)24-13(23)25-11(3)26-12(2)27-9-7(17)5(15)4(14(19,20)21)6(16)8(9)18/h1H3,(H4,22,23,24,25)

Standard InChI Key:  SCAGPVXSZNKRRF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.5225  -24.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089  -24.4565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089  -22.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0906  -23.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907  -24.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060  -24.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791  -23.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059  -22.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018  -23.6280    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062  -24.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121  -25.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317  -25.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2258  -24.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8101  -21.9752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363  -24.4565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3872  -25.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862  -25.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513  -22.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174  -26.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986  -27.2079    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414  -26.5060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0216  -27.2034    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1622  -25.0482    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.9669  -26.4801    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558  -25.0724    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6426  -23.6410    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 12 13  1  0
  1  4  2  0
 13 14  2  0
 14 11  1  0
  2  3  2  0
  4 15  1  0
  3  6  1  0
  2 16  1  0
 17 18  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 19  1  0
  9  5  1  0
 12 20  1  0
  5  4  1  0
 20 21  1  0
  8 10  1  0
 20 22  1  0
  5  6  2  0
 20 23  1  0
 10 11  1  0
 18 24  1  0
 11 18  2  0
 17 25  1  0
 13 26  1  0
 17 12  2  0
 14 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA604722

   5-Methyl-6-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]sulfanylfuro[2,3-d]pyrimidine-2,4-diamine

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: 412.29

Molecular Weight (Monoisotopic): 412.0229

AlogP: 4.42

#Rotatable Bonds: 2

Polar Surface Area: 90.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.07

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -0.65

References

1. Gangjee A, Jain HD, Phan J, Guo X, Queener SF, Kisliuk RL..  (2010)  2,4-Diamino-5-methyl-6-substituted arylthio-furo[2,3-d]pyrimidines as novel classical and nonclassical antifolates as potential dual thymidylate synthase and dihydrofolate reductase inhibitors.,  18  (2): [PMID:20056546] [10.1016/j.bmc.2009.11.029]

Source

Source(1):

• Scientific Literature