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

ID: ALA4227384

PubChem CID: 145968380

Max Phase: Preclinical

Molecular Formula: C17H21N5OS

Molecular Weight: 343.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21N5OS/c1-9(2)22-15-13(14(18)20-17(19)21-15)10(3)16(22)24-12-7-5-6-11(8-12)23-4/h5-9H,1-4H3,(H4,18,19,20,21)

Standard InChI Key:  UMOCMFBMLACMGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   32.2818  -10.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2806  -11.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9887  -11.9097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9869  -10.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5726  -11.9088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9844   -9.4552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6955  -10.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7003  -11.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4803  -11.7447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9577  -11.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4726  -10.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7205   -9.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7749  -11.0747    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.1876  -11.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7807  -12.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1927  -13.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0108  -13.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4150  -12.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0006  -11.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2322  -12.4665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6474  -13.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4747  -12.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7642  -12.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1796  -12.9726    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
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227384

   ---

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: 343.46

Molecular Weight (Monoisotopic): 343.1467

AlogP: 3.64

#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: 7.89

CX LogP: 3.76

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -1.08

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