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

ID: ALA4227977

PubChem CID: 77461251

Max Phase: Preclinical

Molecular Formula: C15H17N5OS

Molecular Weight: 315.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(Sc2c(C)c3c(N)nc(N)nc3n2C)c1

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

Standard InChI Key:  MYBSYTVJQVSHCK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    3.4902  -10.5698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891  -11.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971  -11.7983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1953  -10.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810  -11.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1929   -9.3437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9039  -10.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9087  -11.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888  -11.6333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1661  -10.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6810  -10.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9290   -9.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9833  -10.9633    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.3961  -11.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9891  -12.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4012  -13.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2192  -13.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6235  -12.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2091  -11.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4406  -12.3551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8559  -13.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9458  -12.4090    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
 18 20  1  0
 20 21  1  0
  9 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227977

   6-(3-Methoxyphenyl)sulfanyl-5,7-dimethylpyrrolo[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: 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: -0.97

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