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

ID: ALA191241

PubChem CID: 11186831

Max Phase: Preclinical

Molecular Formula: C17H17N5OS

Molecular Weight: 339.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCCn1c(Sc2cccc(OC)c2)nc2c(N)ncnc21

Standard InChI:  InChI=1S/C17H17N5OS/c1-3-4-5-9-22-16-14(15(18)19-11-20-16)21-17(22)24-13-8-6-7-12(10-13)23-2/h1,6-8,10-11H,4-5,9H2,2H3,(H2,18,19,20)

Standard InChI Key:  VQKBRDXFGLLDPX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.1250    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    2.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    1.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500    1.4083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    1.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292    3.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292    0.6875    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  4  2  0
  7  5  2  0
  8  1  1  0
  9  6  1  0
 10 19  1  0
 11 10  3  0
 12  7  1  0
 13  8  1  0
 14 13  1  0
 15  2  1  0
 16  6  1  0
 17 14  2  0
 18 17  1  0
 19 23  1  0
 20 21  1  0
 21 13  2  0
 22 20  2  0
 23 15  1  0
 24 18  1  0
  4  5  1  0
  9 12  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191241

   8-(3-Methoxy-phenylsulfanyl)-9-pent-4-ynyl-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: 339.42

Molecular Weight (Monoisotopic): 339.1154

AlogP: 2.98

#Rotatable Bonds: 6

Polar Surface Area: 78.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.51

CX LogP: 3.37

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.55

Np Likeness Score: -1.19

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