8-(3-Methoxy-benzenesulfinyl)-9-pent-4-ynyl-9H-purin-6-ylamine

ID: ALA189537

Cas Number: 827302-60-3

PubChem CID: 44400120

Max Phase: Preclinical

Molecular Formula: C17H17N5O2S

Molecular Weight: 355.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCCn1c([S+]([O-])c2cccc(OC)c2)nc2c(N)ncnc21

Standard InChI:  InChI=1S/C17H17N5O2S/c1-3-4-5-9-22-16-14(15(18)19-11-20-16)21-17(22)25(23)13-8-6-7-12(10-13)24-2/h1,6-8,10-11H,4-5,9H2,2H3,(H2,18,19,20)

Standard InChI Key:  IFLJZWIYZHTUMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.1340   -3.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284   -4.2209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8929   -3.0531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4522   -3.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0423   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4137   -2.9867    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2792   -3.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574   -5.1080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6995   -3.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6963   -4.3778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560   -6.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -7.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833   -2.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2844   -5.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4153   -2.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6117   -4.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6927   -2.9454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2687   -3.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -4.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -3.0050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -6.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9952   -4.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728   -4.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7948   -5.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365   -2.1779    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 21  1  0
 12 11  3  0
 13  9  1  0
 14  8  1  0
 15  6  1  0
 16  2  1  0
 17  7  1  0
 18 13  2  0
 19  9  2  0
 20 18  1  0
 21 24  1  0
 22 19  1  0
 23 22  2  0
 24 16  1  0
 25 20  1  0
  4  5  1  0
 10 14  2  0
 23 18  1  0
M  CHG  2   6   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA189537

   8-(3-Methoxybenzene-1-sulfinyl)-9-(pent-4-yn-1-yl)-9H-purin-6-amine

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: 355.42

Molecular Weight (Monoisotopic): 355.1103

AlogP: 2.00

#Rotatable Bonds: 6

Polar Surface Area: 101.91

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.53

CX LogP: 2.00

CX LogD: 2.00

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: -0.56

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