6-(3-Methoxy-phenylsulfanyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA123984

PubChem CID: 5742624

Max Phase: Preclinical

Molecular Formula: C14H15N5OS

Molecular Weight: 301.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(Sc2[nH]c3nc(N)nc(N)c3c2C)c1

Standard InChI:  InChI=1S/C14H15N5OS/c1-7-10-11(15)17-14(16)19-12(10)18-13(7)21-9-5-3-4-8(6-9)20-2/h3-6H,1-2H3,(H5,15,16,17,18,19)

Standard InChI Key:  RKFQENIRKKUKNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.3817   -1.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817   -2.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673   -2.5501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0962   -2.5501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6673   -0.0751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -1.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -2.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682   -2.3925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6832   -1.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682   -1.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132   -0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582   -1.7251    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -2.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582   -3.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -3.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -3.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082   -3.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -2.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3832   -3.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -3.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  2  5  1  0
 11 12  1  0
  2  3  1  0
 10 13  1  0
  4  6  1  0
 13 14  1  0
  7  8  1  0
 14 15  2  0
  3  8  2  0
 15 16  1  0
  1  2  2  0
 16 17  2  0
  7  4  2  0
 17 18  1  0
  4  1  1  0
 18 19  2  0
 19 14  1  0
  8  9  1  0
 20 21  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA123984

   6-(3-methoxyphenyl)sulfanyl-5-methyl-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: 301.38

Molecular Weight (Monoisotopic): 301.0997

AlogP: 2.59

#Rotatable Bonds: 3

Polar Surface Area: 102.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.35

CX Basic pKa: 8.36

CX LogP: 2.77

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -0.78

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. Gangjee A, Lin X, Biondo LR, Queener SF..  (2010)  CoMFA analysis of tgDHFR and rlDHFR based on antifolates with 6-5 fused ring system using the all-orientation search (AOS) routine and a modified cross-validated r(2)-guided region selection (q(2)-GRS) routine and its initial application.,  18  (4): [PMID:20117005] [10.1016/j.bmc.2009.12.066]

3. 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