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

ID: ALA598293

PubChem CID: 46231413

Max Phase: Preclinical

Molecular Formula: C15H16N4O3S

Molecular Weight: 332.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Sc2oc3nc(N)nc(N)c3c2C)cc1OC

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

Standard InChI Key:  NCEGDNXACJCNGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.3156    1.4009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3156    0.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0293    0.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0293    1.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7474    1.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7474    0.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5322    0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0171    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5322    1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8400    0.9887    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2442    0.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0502   -1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4698   -0.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0637    0.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0281    2.6415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020    0.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2253   -1.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8244   -0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7868    2.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8050   -1.8632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9810   -1.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4554   -1.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0367   -2.5910    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
  9 19  1  0
  9  5  1  0
 17 20  1  0
  5  4  1  0
 20 21  1  0
  8 10  1  0
 12 22  1  0
  5  6  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA598293

   6-(3,4-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: -0.65

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