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

ID: ALA611984

PubChem CID: 46231414

Max Phase: Preclinical

Molecular Formula: C17H20N4OS

Molecular Weight: 328.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(C)C)c1Sc1oc2nc(N)nc(N)c2c1C

Standard InChI:  InChI=1S/C17H20N4OS/c1-8(2)11-7-5-6-9(3)13(11)23-16-10(4)12-14(18)20-17(19)21-15(12)22-16/h5-8H,1-4H3,(H4,18,19,20,21)

Standard InChI Key:  FRCJZUGCJHVMGL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.4237   -5.1974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4237   -6.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092   -6.4395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092   -4.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -5.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -6.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -6.2786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -5.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2046   -4.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -5.6100    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -6.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3162   -7.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7363   -7.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3299   -6.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7103   -3.9553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381   -6.4395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905   -7.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0890   -7.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496   -4.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7359   -7.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473   -5.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5723   -5.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3398   -4.9057    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
 18 20  1  0
  5  4  1  0
 14 21  1  0
  8 10  1  0
 21 22  1  0
  5  6  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA611984

   5-Methyl-6-(2-methyl-6-propan-2-ylphenyl)sulfanylfuro[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: 328.44

Molecular Weight (Monoisotopic): 328.1358

AlogP: 4.28

#Rotatable Bonds: 3

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: 4.74

CX LogD: 4.74

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