9-Butyl-8-(3,4,5-trimethoxy-benzenesulfinyl)-9H-purin-6-ylamine

ID: ALA192761

Cas Number: 827302-62-5

PubChem CID: 44400031

Max Phase: Preclinical

Molecular Formula: C18H23N5O4S

Molecular Weight: 405.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c([S+]([O-])c2cc(OC)c(OC)c(OC)c2)nc2c(N)ncnc21

Standard InChI:  InChI=1S/C18H23N5O4S/c1-5-6-7-23-17-14(16(19)20-10-21-17)22-18(23)28(24)11-8-12(25-2)15(27-4)13(9-11)26-3/h8-10H,5-7H2,1-4H3,(H2,19,20,21)

Standard InChI Key:  LFRDOBXEBOUJJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.1348   -3.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2307   -4.2181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968   -3.0498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4539   -3.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0431   -4.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -2.9858    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6991   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -3.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4600   -5.1070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -4.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7082   -4.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -2.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2670   -3.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9931   -4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6987   -4.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2878   -5.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4144   -2.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6129   -4.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6962   -2.9472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5646   -4.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5385   -3.0053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0079   -5.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8440   -4.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -2.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2907   -5.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7956   -5.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778   -6.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -6.9585    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  6  1  0
  8  4  2  0
  9  5  2  0
 10 13  1  0
 11  7  2  0
 12  7  1  0
 13 12  2  0
 14 11  1  0
 15  8  1  0
 16  9  1  0
 17  6  1  0
 18  2  1  0
 19  8  1  0
 20 10  1  0
 21 13  1  0
 22 14  1  0
 23 20  1  0
 24 21  1  0
 25 22  1  0
 26 18  1  0
 27 26  1  0
 28 27  1  0
  4  5  1  0
 14 10  2  0
 15 16  2  0
M  CHG  2   6   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA192761

   9-Butyl-8-(3,4,5-trimethoxybenzene-1-sulfinyl)-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: 405.48

Molecular Weight (Monoisotopic): 405.1471

AlogP: 2.40

#Rotatable Bonds: 8

Polar Surface Area: 120.37

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.53

CX LogP: 2.04

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -0.30

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