6-((2-Methoxyphenyl)thio)-5,7-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4227112

PubChem CID: 145968368

Max Phase: Preclinical

Molecular Formula: C15H17N5OS

Molecular Weight: 315.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1Sc1c(C)c2c(N)nc(N)nc2n1C

Standard InChI:  InChI=1S/C15H17N5OS/c1-8-11-12(16)18-15(17)19-13(11)20(2)14(8)22-10-7-5-4-6-9(10)21-3/h4-7H,1-3H3,(H4,16,17,18,19)

Standard InChI Key:  OXBQXSXKYSCHQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   12.7724  -23.6242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7712  -24.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4793  -24.8527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4775  -23.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0632  -24.8518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4750  -22.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1861  -23.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1909  -24.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9709  -24.6877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4483  -24.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9632  -23.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2111  -22.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2654  -24.0177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6782  -24.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2713  -25.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6833  -26.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5014  -26.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9056  -25.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4912  -24.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8930  -24.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7101  -23.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2280  -25.4634    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 18  1  0
 18 19  2  0
 19 14  1  0
 19 20  1  0
 20 21  1  0
  9 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227112

   ---

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: 315.40

Molecular Weight (Monoisotopic): 315.1154

AlogP: 2.60

#Rotatable Bonds: 3

Polar Surface Area: 91.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.96

CX LogP: 2.99

CX LogD: 2.34

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -0.86

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