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

ID: ALA596673

PubChem CID: 46231370

Max Phase: Preclinical

Molecular Formula: C17H14N4OS

Molecular Weight: 322.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc3ccccc3c2)oc2nc(N)nc(N)c12

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

Standard InChI Key:  IIQMDNNJGHZXKR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    8.5893   -7.5627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5893   -8.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3039   -8.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3039   -7.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0229   -7.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0229   -8.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8085   -8.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2941   -7.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8085   -7.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0635   -6.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1191   -7.9757    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.5316   -7.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5273   -5.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1186   -6.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3027   -6.3205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749   -8.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3584   -7.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3566   -5.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7650   -6.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5862   -6.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9999   -5.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5863   -5.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7666   -5.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0
 11 12  1  0
 12 17  2  0
  1  2  1  0
 18 13  1  0
  1  4  2  0
 13 14  2  0
 14 12  1  0
  2  3  2  0
  4 15  1  0
  3  6  1  0
  2 16  1  0
 19 17  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  5  4  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  2  0
 22 23  1  0
 23 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA596673

   2,4-Diamino-5-methyl-6-(2-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: -0.75

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