(1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(2-(trimethylsilyl)ethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

ID: ALA257405

PubChem CID: 44449058

Max Phase: Preclinical

Molecular Formula: C25H29ClN6O3Si

Molecular Weight: 525.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NCc4cccc(Cl)c4)nc(C#C[Si](C)(C)C)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C25H29ClN6O3Si/c1-27-24(35)25-11-16(25)19(20(33)21(25)34)32-13-29-18-22(28-12-14-6-5-7-15(26)10-14)30-17(31-23(18)32)8-9-36(2,3)4/h5-7,10,13,16,19-21,33-34H,11-12H2,1-4H3,(H,27,35)(H,28,30,31)/t16-,19-,20+,21+,25+/m1/s1

Standard InChI Key:  RDYPNVDYKVTREJ-YZSDQEEOSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  1  0  0  0  0  0999 V2000
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    2.6002  -21.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570  -20.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225  -20.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943  -20.5202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506  -21.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057  -20.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6414  -20.2157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518  -22.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843  -21.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156  -19.4296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906  -19.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715  -20.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030  -20.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884  -21.5163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1416  -21.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8102  -21.3638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215  -20.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3879  -20.0603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5225  -20.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846  -19.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4357  -19.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109  -19.4522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1424  -20.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8088  -19.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5614  -20.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2274  -19.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1396  -18.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801  -18.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173  -19.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9817  -20.0919    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2286  -22.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153  -23.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4052  -24.3098    0.0000 Si  0  0  0  0  0  4  0  0  0  0  0  0
    5.4406  -25.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2254  -24.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851  -24.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  1
 17 18  2  0
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 18 19  1  0
 21 20  1  0
 22 21  1  0
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  1  9  1  6
 20  4  1  1
  2 10  1  6
  8 14  1  0
 21 23  1  1
 19 24  1  0
  4  5  1  0
 24 25  1  0
 13 11  1  0
 25 26  2  0
 11 12  2  0
 26 27  1  0
 12  8  1  0
 27 28  2  0
  2  3  1  0
 28 29  1  0
  4  6  2  0
 29 30  2  0
 30 25  1  0
 13 14  2  0
 27 31  1  0
  3 21  1  0
 16 32  1  0
 14 15  1  0
 32 33  3  0
  5  7  1  0
 33 34  1  0
 15 16  2  0
 34 35  1  0
 20  1  1  0
 34 36  1  0
 16 17  1  0
 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA257405

   (1S,2R,3S,4R,5S)-4-[6-[(3-chlorophenyl)methylamino]-2-(2-trimethylsilylethynyl)purin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

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: 525.09

Molecular Weight (Monoisotopic): 524.1759

AlogP: ┄

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HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

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CX LogD: ┄

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QED Weighted: ┄

Np Likeness Score: ┄

References

1. Melman A, Gao ZG, Kumar D, Wan TC, Gizewski E, Auchampach JA, Jacobson KA..  (2008)  Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.,  18  (9): [PMID:18424135] [10.1016/j.bmcl.2008.04.001]

Source

Source(1):

• Scientific Literature