7-Ethyl-6-((3-methoxyphenyl)thio)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4227124

PubChem CID: 124080837

Max Phase: Preclinical

Molecular Formula: C16H19N5OS

Molecular Weight: 329.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c(Sc2cccc(OC)c2)c(C)c2c(N)nc(N)nc21

Standard InChI:  InChI=1S/C16H19N5OS/c1-4-21-14-12(13(17)19-16(18)20-14)9(2)15(21)23-11-7-5-6-10(8-11)22-3/h5-8H,4H2,1-3H3,(H4,17,18,19,20)

Standard InChI Key:  ULDSMDKWSKBCEI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   13.7753  -10.8504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7741  -11.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4822  -12.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4804  -10.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0661  -12.0780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4779   -9.6244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1890  -10.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1938  -11.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9738  -11.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4512  -11.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9661  -10.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2140   -9.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2684  -11.2440    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.6811  -11.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2742  -12.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6862  -13.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5043  -13.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9085  -12.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4941  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7257  -12.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1409  -13.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2309  -12.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6876  -13.3001    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
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227124

   ---

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: 329.43

Molecular Weight (Monoisotopic): 329.1310

AlogP: 3.08

#Rotatable Bonds: 4

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: 7.93

CX LogP: 3.35

CX LogD: 2.72

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -1.06

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