5-Methyl-6-(naphthalen-1-ylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA122998

PubChem CID: 5742617

Max Phase: Preclinical

Molecular Formula: C17H15N5S

Molecular Weight: 321.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2cccc3ccccc23)[nH]c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C17H15N5S/c1-9-13-14(18)20-17(19)22-15(13)21-16(9)23-12-8-4-6-10-5-2-3-7-11(10)12/h2-8H,1H3,(H5,18,19,20,21,22)

Standard InChI Key:  FHGCNTCLPBNZQO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    3.7292   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -3.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -3.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -2.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -2.9000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -3.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -1.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -3.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -4.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  8  1  0
  4  1  1  0
  5  2  1  0
  6  7  2  0
  7  3  1  0
  8  1  2  0
  9  5  2  0
 10  1  1  0
 11 10  1  0
 12 11  1  0
 13  7  1  0
 14  9  1  0
 15 12  1  0
 16  8  1  0
 17 11  2  0
 18 17  1  0
 19 12  2  0
 20 18  2  0
 21 15  2  0
 22 19  1  0
 23 22  2  0
  3  2  2  0
  6  9  1  0
 15 20  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA122998

   5-methyl-6-(1-naphthylsulfanyl)-7H-pyrrolo[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: 321.41

Molecular Weight (Monoisotopic): 321.1048

AlogP: 3.74

#Rotatable Bonds: 2

Polar Surface Area: 93.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.34

CX Basic pKa: 8.36

CX LogP: 3.91

CX LogD: 2.93

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: -0.64

References

1. Gangjee A, Lin X, Queener SF..  (2004)  Design, synthesis, and biological evaluation of 2,4-diamino-5-methyl-6-substituted-pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors.,  47  (14): [PMID:15214795] [10.1021/jm0306327]

2. 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