9-(2-Isopropoxy-ethyl)-8-(3-methoxy-benzenesulfinyl)-9H-purin-6-ylamine

ID: ALA193672

PubChem CID: 44400127

Max Phase: Preclinical

Molecular Formula: C17H21N5O3S

Molecular Weight: 375.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc([S+]([O-])c2nc3c(N)ncnc3n2CCOC(C)C)c1

Standard InChI:  InChI=1S/C17H21N5O3S/c1-11(2)25-8-7-22-16-14(15(18)19-10-20-16)21-17(22)26(23)13-6-4-5-12(9-13)24-3/h4-6,9-11H,7-8H2,1-3H3,(H2,18,19,20)

Standard InChI Key:  VYMNYUOAXXFCKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.1349   -3.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2272   -4.2238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -3.0548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4508   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0403   -4.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -2.9844    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825   -3.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4573   -5.1122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987   -3.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6959   -4.3851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849   -2.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2853   -5.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4151   -2.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -4.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7003   -2.9459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2699   -3.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891   -5.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120   -4.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353   -3.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -6.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969   -4.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2717   -4.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3588   -6.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293   -2.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412   -7.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1446   -7.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  4  2  0
  8  5  2  0
  9  6  1  0
 10  7  1  0
 11  9  1  0
 12  8  1  0
 13  6  1  0
 14  2  1  0
 15  7  1  0
 16 11  2  0
 17 14  1  0
 18  9  2  0
 19 16  1  0
 20 17  1  0
 21 18  1  0
 22 21  2  0
 23 20  1  0
 24 19  1  0
 25 23  1  0
 26 23  1  0
  4  5  1  0
 10 12  2  0
 22 16  1  0
M  CHG  2   6   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA193672

   9-(2-Isopropoxy-ethyl)-8-(3-methoxy-benzenesulfinyl)-9H-purin-6-ylamine

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: 375.45

Molecular Weight (Monoisotopic): 375.1365

AlogP: 2.01

#Rotatable Bonds: 7

Polar Surface Area: 111.14

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.47

CX LogP: 1.76

CX LogD: 1.76

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.78

References

1. Llauger L, He H, Kim J, Aguirre J, Rosen N, Peters U, Davies P, Chiosis G..  (2005)  Evaluation of 8-arylsulfanyl, 8-arylsulfoxyl, and 8-arylsulfonyl adenine derivatives as inhibitors of the heat shock protein 90.,  48  (8): [PMID:15828828] [10.1021/jm049012b]

Source

Source(1):

• Scientific Literature