Diamino-5-isopropyl-6-(2'-naphthylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA477150

PubChem CID: 24950853

Max Phase: Preclinical

Molecular Formula: C19H19N5S

Molecular Weight: 349.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1c(Sc2ccc3ccccc3c2)[nH]c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C19H19N5S/c1-10(2)14-15-16(20)22-19(21)24-17(15)23-18(14)25-13-8-7-11-5-3-4-6-12(11)9-13/h3-10H,1-2H3,(H5,20,21,22,23,24)

Standard InChI Key:  FVTLWDMKFHXFCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.6819  -12.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807  -13.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3956  -14.0985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3938  -12.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091  -12.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1094  -13.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8999  -13.9423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3882  -13.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8982  -12.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9660  -14.0976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3913  -11.6205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2097  -13.2658    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6122  -13.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1868  -14.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5886  -15.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4325  -13.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2651  -11.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8079  -11.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0884  -11.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8368  -14.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4149  -15.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155  -16.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6397  -16.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0615  -15.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6593  -14.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
 15 21  2  0
  5  4  2  0
 20 16  2  0
 16 13  1  0
  6  7  1  0
  9 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 17 19  1  0
 20 21  1  0
  9  5  1  0
  4  1  1  0
  2 10  1  0
  5  6  1  0
  4 11  1  0
 20 25  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA477150

   -Diamino-5-isopropyl-6-(2''-naphthylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine

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: 349.46

Molecular Weight (Monoisotopic): 349.1361

AlogP: 4.55

#Rotatable Bonds: 3

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: 12.13

CX Basic pKa: 8.33

CX LogP: 4.64

CX LogD: 3.69

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -0.53

References

1. Gangjee A, Jain HD, Queener SF, Kisliuk RL..  (2008)  The effect of 5-alkyl modification on the biological activity of pyrrolo[2,3-d]pyrimidine containing classical and nonclassical antifolates as inhibitors of dihydrofolate reductase and as antitumor and/or antiopportunistic infection agents.,  51  (15): [PMID:18605720] [10.1021/jm800244v]

Source

Source(1):

• Scientific Literature