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

ID: ALA596681

PubChem CID: 46231373

Max Phase: Preclinical

Molecular Formula: C15H16N4O3S

Molecular Weight: 332.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(Sc2oc3nc(N)nc(N)c3c2C)c1

Standard InChI:  InChI=1S/C15H16N4O3S/c1-7-11-12(16)18-15(17)19-13(11)22-14(7)23-10-6-8(20-2)4-5-9(10)21-3/h4-6H,1-3H3,(H4,16,17,18,19)

Standard InChI Key:  KOULRJAJSBRSFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -2.8383  -17.6116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8383  -18.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247  -18.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247  -17.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4065  -17.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066  -18.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6219  -18.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368  -18.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218  -17.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6859  -18.0237    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0903  -18.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962  -20.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158  -19.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098  -18.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259  -16.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5521  -18.8522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713  -20.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6703  -19.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537  -19.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672  -16.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734  -20.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1398  -19.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466  -20.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  9 20  1  0
  5  4  1  0
 19 21  1  0
  8 10  1  0
 13 22  1  0
  5  6  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA596681

   6-(2,5-Dimethoxyphenyl)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: 332.39

Molecular Weight (Monoisotopic): 332.0943

AlogP: 2.86

#Rotatable Bonds: 4

Polar Surface Area: 109.42

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.07

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.56

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