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

ID: ALA190654

Cas Number: 827302-63-6

PubChem CID: 44399994

Max Phase: Preclinical

Molecular Formula: C18H23N5O5S

Molecular Weight: 421.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H23N5O5S/c1-5-6-7-23-17-14(16(19)20-10-21-17)22-18(23)29(24,25)11-8-12(26-2)15(28-4)13(9-11)27-3/h8-10H,5-7H2,1-4H3,(H2,19,20,21)

Standard InChI Key:  HCIBJWRRCCOAEZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.3616   -8.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0746   -9.3171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0727   -7.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7909   -8.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961   -8.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886   -9.1563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733   -8.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802   -7.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0688   -6.8386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8984   -8.4752    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7190   -8.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8935   -7.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9076   -9.3002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8484   -9.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3001  -10.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599  -11.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0116  -11.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1314   -9.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513   -9.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3584   -8.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9398   -7.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1213   -7.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3451   -7.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9262   -6.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1808   -8.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5885   -7.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3646   -9.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1896   -9.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  2  0
  1  2  2  0
  7 15  1  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 12 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  4 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 12  1  0
  8 11  1  0
 24 25  1  0
 22 24  1  0
 11 12  1  0
  2  3  1  0
 26 27  1  0
 21 26  1  0
 11 13  2  0
  3  6  2  0
 28 29  1  0
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA190654

   9-Butyl-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: 421.48

Molecular Weight (Monoisotopic): 421.1420

AlogP: 2.07

#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: 2.18

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -0.59

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. Gundla R, Kazemi R, Sanam R, Muttineni R, Sarma JA, Dayam R, Neamati N..  (2008)  Discovery of novel small-molecule inhibitors of human epidermal growth factor receptor-2: combined ligand and target-based approach.,  51  (12): [PMID:18500794] [10.1021/jm7013875]

Source

Source(1):

• Scientific Literature