9-Pent-4-ynyl-8-(2-trifluoromethoxy-phenylsulfanyl)-9H-purin-6-ylamine

ID: ALA371372

PubChem CID: 11463506

Max Phase: Preclinical

Molecular Formula: C17H14F3N5OS

Molecular Weight: 393.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCCn1c(Sc2ccccc2OC(F)(F)F)nc2c(N)ncnc21

Standard InChI:  InChI=1S/C17H14F3N5OS/c1-2-3-6-9-25-15-13(14(21)22-10-23-15)24-16(25)27-12-8-5-4-7-11(12)26-17(18,19)20/h1,4-5,7-8,10H,3,6,9H2,(H2,21,22,23)

Standard InChI Key:  KMLKYPXEIVGNDC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  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
    2.9500    1.4083    0.0000 S   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
    5.4250    1.4083    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
   -0.5750    1.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000    1.4083    0.0000 O   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
    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
    4.1875    0.6958    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
    1.8917   -0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    1.4083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167    0.5833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292    2.2333    0.0000 F   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
    1.5917   -1.4417    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
    4.5917   -0.0167    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
    4.1792   -0.7375    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  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  4  2  0
  8 11  1  0
  9  5  2  0
 10  7  1  0
 11 15  1  0
 12  6  1  0
 13 22  1  0
 14 13  3  0
 15 12  1  0
 16  9  1  0
 17  2  1  0
 18  8  1  0
 19  8  1  0
 20  8  1  0
 21  7  1  0
 22 25  1  0
 23 12  2  0
 24 15  2  0
 25 17  1  0
 26 27  2  0
 27 23  1  0
  4  5  1  0
 10 16  2  0
 26 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA371372

   9-Pent-4-ynyl-8-(2-trifluoromethoxy-phenylsulfanyl)-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: 393.39

Molecular Weight (Monoisotopic): 393.0871

AlogP: 3.87

#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: 4.96

CX LogD: 4.96

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.28

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]

2. Patel HJ, Patel PD, Ochiana SO, Yan P, Sun W, Patel MR, Shah SK, Tramentozzi E, Brooks J, Bolaender A, Shrestha L, Stephani R, Finotti P, Leifer C, Li Z, Gewirth DT, Taldone T, Chiosis G..  (2015)  Structure-activity relationship in a purine-scaffold compound series with selectivity for the endoplasmic reticulum Hsp90 paralog Grp94.,  58  (9): [PMID:25901531] [10.1021/acs.jmedchem.5b00197]

Source

Source(1):

• Scientific Literature