2,4-Diamino-5-methyl-6-(1-naphthylthio)furo[2,3-d]pyrimidine

ID: ALA602104

PubChem CID: 46231369

Max Phase: Preclinical

Molecular Formula: C17H14N4OS

Molecular Weight: 322.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2cccc3ccccc23)oc2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C17H14N4OS/c1-9-13-14(18)20-17(19)21-15(13)22-16(9)23-12-8-4-6-10-5-2-3-7-11(10)12/h2-8H,1H3,(H4,18,19,20,21)

Standard InChI Key:  WWGMCCMWXAGEOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.8142   -7.5579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8142   -8.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -8.8001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -7.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3806   -7.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807   -8.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951   -8.6394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1095   -7.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -7.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3401   -6.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -7.9711    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281   -7.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -5.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238   -5.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -6.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009   -6.3159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287   -8.8001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3656   -6.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -7.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616   -7.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -7.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -7.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1832   -6.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0
 11 12  1  0
 12 19  2  0
  1  2  1  0
 18 13  2  0
  1  4  2  0
 13 14  1  0
  2  3  2  0
 14 15  2  0
 15 12  1  0
  3  6  1  0
  4 16  1  0
  6  7  1  0
  2 17  1  0
 18 19  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  5  4  1  0
  9 10  1  0
  5  6  2  0
 18 23  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA602104

   2,4-Diamino-5-methyl-6-(1-naphthylthio)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: 322.39

Molecular Weight (Monoisotopic): 322.0888

AlogP: 4.00

#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: 3.97

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.71

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