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

ID: ALA4228488

PubChem CID: 145970467

Max Phase: Preclinical

Molecular Formula: C18H23N5OS

Molecular Weight: 357.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c(Sc2cccc(OC)c2)c(C)c2c(N)nc(N)nc21

Standard InChI:  InChI=1S/C18H23N5OS/c1-4-5-9-23-16-14(15(19)21-18(20)22-16)11(2)17(23)25-13-8-6-7-12(10-13)24-3/h6-8,10H,4-5,9H2,1-3H3,(H4,19,20,21,22)

Standard InChI Key:  HDNKCXNGZLCJHM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   40.8210  -10.1075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.8199  -10.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5279  -11.3360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5261   -9.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1118  -11.3351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5237   -8.8815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2347  -10.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2395  -10.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0196  -11.1710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.4969  -10.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0118   -9.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2598   -9.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3141  -10.5011    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   44.7269  -11.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3199  -11.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7320  -12.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5500  -12.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9543  -11.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5399  -11.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7714  -11.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   47.1867  -12.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2766  -11.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7333  -12.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9904  -13.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4471  -13.9434    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
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228488

   ---

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: 357.48

Molecular Weight (Monoisotopic): 357.1623

AlogP: 3.86

#Rotatable Bonds: 6

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: 7.92

CX LogP: 4.31

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -1.03

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