5,7-Dimethyl-6-(naphthalen-1-ylthio)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4229284

PubChem CID: 145988837

Max Phase: Preclinical

Molecular Formula: C18H17N5S

Molecular Weight: 335.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2cccc3ccccc23)n(C)c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C18H17N5S/c1-10-14-15(19)21-18(20)22-16(14)23(2)17(10)24-13-9-5-7-11-6-3-4-8-12(11)13/h3-9H,1-2H3,(H4,19,20,21,22)

Standard InChI Key:  MKXXVXGKECMIDT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   36.9332  -23.0670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9320  -23.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6442  -24.3038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6424  -22.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2198  -24.3029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6400  -21.8369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3551  -23.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3599  -23.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1441  -24.1388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6215  -23.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1363  -22.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3843  -22.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4428  -23.4647    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.8596  -24.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4486  -24.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8648  -25.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6869  -25.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4011  -24.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6768  -24.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0893  -24.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9031  -24.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3053  -24.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8838  -23.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0713  -23.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  2  5  1  0
  4  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 20  1  0
 19 14  1  0
  9 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4229284

   ---

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: 335.44

Molecular Weight (Monoisotopic): 335.1205

AlogP: 3.75

#Rotatable Bonds: 2

Polar Surface Area: 82.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.95

CX LogP: 4.14

CX LogD: 3.50

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -0.85

References

1. Shah K, Lin X, Queener SF, Cody V, Pace J, Gangjee A..  (2018)  Targeting species specific amino acid residues: Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors and potential anti-opportunistic infection agents.,  26  (9): [PMID:29691153] [10.1016/j.bmc.2018.04.032]

Source

Source(1):

• Scientific Literature