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

ID: ALA597885

PubChem CID: 46231409

Max Phase: Preclinical

Molecular Formula: C14H14N4O2S

Molecular Weight: 302.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Sc2oc3nc(N)nc(N)c3c2C)cc1

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

Standard InChI Key:  NWDZABZKWUKYGL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    7.7641  -17.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7641  -18.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4776  -18.5906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4776  -16.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1959  -17.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1957  -18.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9804  -18.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4655  -17.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9805  -17.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2882  -17.7622    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.6925  -18.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4984  -19.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9180  -19.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5120  -18.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4764  -16.1094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0503  -18.5906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6735  -19.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2726  -19.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2351  -16.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9036  -20.6321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4849  -21.3418    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
 12 20  1  0
  5  4  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA597885

   2,4-Diamino-5-methyl-6-(4''-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: -0.77

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