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

ID: ALA598292

PubChem CID: 46231412

Max Phase: Preclinical

Molecular Formula: C14H14N4O2S

Molecular Weight: 302.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(Sc2oc3nc(N)nc(N)c3c2C)c1

Standard InChI:  InChI=1S/C14H14N4O2S/c1-7-10-11(15)17-14(16)18-12(10)20-13(7)21-9-5-3-4-8(6-9)19-2/h3-6H,1-2H3,(H4,15,16,17,18)

Standard InChI Key:  HFIVKEUYLXPISD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.7631    1.5336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7631    0.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312    1.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312    0.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466    0.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    1.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465    1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2389    1.1214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9714   -1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910   -0.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9850    0.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0505    2.7742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    0.2930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -1.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -0.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    2.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2738   -1.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -1.7209    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
  9 19  1  0
  9  5  1  0
 17 20  1  0
  5  4  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA598292

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

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: 302.36

Molecular Weight (Monoisotopic): 302.0837

AlogP: 2.86

#Rotatable Bonds: 3

Polar Surface Area: 100.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.07

CX LogP: 2.83

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: -0.83

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