5,7-Dimethyl-6-(naphthalen-2-ylthio)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4227373

PubChem CID: 145967911

Max Phase: Preclinical

Molecular Formula: C18H17N5S

Molecular Weight: 335.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc3ccccc3c2)n(C)c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C18H17N5S/c1-10-14-15(19)21-18(20)22-16(14)23(2)17(10)24-13-8-7-11-5-3-4-6-12(11)9-13/h3-9H,1-2H3,(H4,19,20,21,22)

Standard InChI Key:  HOZSLDLWHVQRPQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   29.7311  -23.4055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7300  -24.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4380  -24.6340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4362  -22.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0220  -24.6330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4338  -22.1794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1449  -23.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1497  -24.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9297  -24.4689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4071  -23.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9219  -23.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1699  -22.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2242  -23.7990    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.6370  -24.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2300  -25.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6421  -25.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4500  -24.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1867  -25.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8644  -25.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4601  -25.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8766  -26.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6972  -26.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0996  -25.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6808  -25.1887    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 20  2  0
 19 17  2  0
 17 14  1  0
  9 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227373

   ---

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: 335.44

Molecular Weight (Monoisotopic): 335.1205

AlogP: 3.75

#Rotatable Bonds: 2

Polar Surface Area: 82.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.95

CX LogP: 4.14

CX LogD: 3.50

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -0.88

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