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

ID: ALA4226465

PubChem CID: 124080838

Max Phase: Preclinical

Molecular Formula: C15H17N5OS

Molecular Weight: 315.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Sc2c(C)c3c(N)nc(N)nc3n2C)cc1

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

Standard InChI Key:  OKWZEJPRXOZLRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   21.9637  -23.6201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9625  -24.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6706  -24.8486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6688  -23.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2545  -24.8477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6664  -22.3940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3774  -23.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3822  -24.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1623  -24.6836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6396  -24.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1545  -23.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4025  -22.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4568  -24.0136    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.8695  -24.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4626  -25.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8747  -26.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6927  -26.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0970  -25.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6825  -24.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4193  -25.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1064  -26.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7029  -27.5435    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
  9 20  1  0
 17 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4226465

   ---

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: 7.95

CX LogP: 2.99

CX LogD: 2.35

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -0.92

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