9-Pent-4-ynyl-8-(3,4,5-trimethoxy-benzenesulfonyl)-9H-purin-6-ylamine

ID: ALA193310

Cas Number: 827302-66-9

PubChem CID: 44400130

Max Phase: Preclinical

Molecular Formula: C19H21N5O5S

Molecular Weight: 431.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCCn1c(S(=O)(=O)c2cc(OC)c(OC)c(OC)c2)nc2c(N)ncnc21

Standard InChI:  InChI=1S/C19H21N5O5S/c1-5-6-7-8-24-18-15(17(20)21-11-22-18)23-19(24)30(25,26)12-9-13(27-2)16(29-4)14(10-12)28-3/h1,9-11H,6-8H2,2-4H3,(H2,20,21,22)

Standard InChI Key:  QCCUXARSTIGMJB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
    4.1875   -0.4917    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
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    3.3625   -0.4917    0.0000 C   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
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    0.1375    3.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -1.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -1.2000    0.0000 O   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 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
    5.4167   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -1.9167    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
  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 13  1  0
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 14 11  1  0
 15  8  1  0
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 17  3  2  0
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 19 18  3  0
 20  9  1  0
 21  2  1  0
 22  8  1  0
 23 10  1  0
 24 14  1  0
 25 13  1  0
 26 27  1  0
 27 21  1  0
 28 23  1  0
 29 24  1  0
 30 25  1  0
  5  6  1  0
 14 10  2  0
 15 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA193310

   9-(Pent-4-yn-1-yl)-8-(3,4,5-trimethoxybenzene-1-sulfonyl)-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: 431.47

Molecular Weight (Monoisotopic): 431.1263

AlogP: 1.68

#Rotatable Bonds: 8

Polar Surface Area: 131.45

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.22

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -0.57

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