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

ID: ALA362972

PubChem CID: 44400093

Max Phase: Preclinical

Molecular Formula: C17H21N5O4S

Molecular Weight: 391.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(S(=O)(=O)c2nc3c(N)ncnc3n2CCOC(C)C)c1

Standard InChI:  InChI=1S/C17H21N5O4S/c1-11(2)26-8-7-22-16-14(15(18)19-10-20-16)21-17(22)27(23,24)13-6-4-5-12(9-13)25-3/h4-6,9-11H,7-8H2,1-3H3,(H2,18,19,20)

Standard InChI Key:  FHYGDELHNKRLBR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.1292    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417    0.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    1.6458    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417    2.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    0.8208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    2.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625    2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375    0.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    3.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292    0.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000   -1.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  4  1  0
  6  2  1  0
  7  3  1  0
  8  5  2  0
  9  6  2  0
 10  8  1  0
 11  3  2  0
 12  3  2  0
 13  7  1  0
 14  9  1  0
 15  2  1  0
 16  8  1  0
 17 13  2  0
 18  7  2  0
 19 15  1  0
 20 17  1  0
 21 19  1  0
 22 18  1  0
 23 22  2  0
 24 21  1  0
 25 20  1  0
 26 24  1  0
 27 24  1  0
  5  6  1  0
 10 14  2  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA362972

   9-(2-Isopropoxy-ethyl)-8-(3-methoxy-benzenesulfonyl)-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: 391.45

Molecular Weight (Monoisotopic): 391.1314

AlogP: 1.67

#Rotatable Bonds: 7

Polar Surface Area: 122.22

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.15

CX LogP: 1.90

CX LogD: 1.90

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -1.25

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