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

ID: ALA4228228

PubChem CID: 145971179

Max Phase: Preclinical

Molecular Formula: C17H21N5OS

Molecular Weight: 343.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(Sc2cccc(OC)c2)c(C)c2c(N)nc(N)nc21

Standard InChI:  InChI=1S/C17H21N5OS/c1-4-8-22-15-13(14(18)20-17(19)21-15)10(2)16(22)24-12-7-5-6-11(9-12)23-3/h5-7,9H,4,8H2,1-3H3,(H4,18,19,20,21)

Standard InChI Key:  FJMFWPUOJWKBOY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   22.7231  -10.7060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7220  -11.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4300  -11.9345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4282  -10.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0139  -11.9336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4258   -9.4799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1368  -10.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1416  -11.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9217  -11.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3990  -11.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9139  -10.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1619   -9.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2162  -11.0995    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.6290  -11.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2220  -12.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6341  -13.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4521  -13.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8564  -12.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4420  -11.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6735  -12.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0888  -13.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1787  -12.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6354  -13.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8925  -13.9313    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
M  END

Alternative Forms

1. Parent:

   

   ALA4228228

   ---

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: 3.47

#Rotatable Bonds: 5

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: 3.87

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -1.09

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