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

ID: ALA609896

PubChem CID: 46231371

Max Phase: Preclinical

Molecular Formula: C15H16N4OS

Molecular Weight: 300.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C)c1Sc1oc2nc(N)nc(N)c2c1C

Standard InChI:  InChI=1S/C15H16N4OS/c1-7-5-4-6-8(2)11(7)21-14-9(3)10-12(16)18-15(17)19-13(10)20-14/h4-6H,1-3H3,(H4,16,17,18,19)

Standard InChI Key:  QYJAHVUNGITYRR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -2.4038  -12.5137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038  -13.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901  -13.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901  -12.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718  -12.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718  -13.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870  -13.5940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2981  -12.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869  -12.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210  -12.9259    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254  -13.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314  -15.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511  -14.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451  -13.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912  -11.2729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1176  -13.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065  -15.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1054  -14.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813  -14.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621  -12.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678  -11.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  1  0
  5  6  2  0
 10 11  1  0
 11 18  2  0
 17 12  2  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
 18 19  1  0
  9  5  1  0
 14 20  1  0
  5  4  1  0
  9 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA609896

   6-(2,6-Dimethylphenyl)sulfanyl-5-methylfuro[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: 300.39

Molecular Weight (Monoisotopic): 300.1045

AlogP: 3.46

#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: 4.01

CX LogD: 4.01

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.75

Np Likeness Score: -0.54

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