5-{(R)-2-[(R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid trimethylsilanylmethyl ester

ID: ALA418302

PubChem CID: 44300807

Max Phase: Preclinical

Molecular Formula: C24H30ClNO7Si

Molecular Weight: 508.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Cc1ccc2c(c1)OC(C(=O)O)(C(=O)OC[Si](C)(C)C)O2)NC[C@H](O)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C24H30ClNO7Si/c1-15(26-13-19(27)17-6-5-7-18(25)12-17)10-16-8-9-20-21(11-16)33-24(32-20,22(28)29)23(30)31-14-34(2,3)4/h5-9,11-12,15,19,26-27H,10,13-14H2,1-4H3,(H,28,29)/t15-,19+,24?/m1/s1

Standard InChI Key:  BMSWKNZUIZEAHU-MXZBBBRTSA-N

Molfile:  

     RDKit          2D

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    7.3500   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -2.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -3.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7292   -2.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4417   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5250   -1.1292    0.0000 Si  0  0  0  0  0  4  0  0  0  0  0  0
    5.2625   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7292   -3.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -4.4792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9667   -1.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6125   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3292   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 25 22  1  0
 20 26  1  1
 27 23  1  0
 28  9  2  0
 29 28  1  0
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 31 17  1  0
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 33 29  2  0
 27 34  1  1
  6  7  1  0
 24 15  2  0
 22 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA418302

   5-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2-(trimethylsilylmethoxycarbonyl)-1,3-benzodioxole-2-carboxylic acid

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: 508.04

Molecular Weight (Monoisotopic): 507.1480

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References

1. Sum FW, Gilbert A, Venkatesan AM, Lim K, Wong V, O'Dell M, Francisco G, Chen Z, Grosu G, Baker J, Ellingboe J, Malamas M, Gunawan I, Primeau J, Largis E, Steiner K..  (1999)  Prodrugs of CL316243: a selective beta3-adrenergic receptor agonist for treating obesity and diabetes.,  9  (14): [PMID:10450954] [10.1016/s0960-894x(99)00316-9]

Source

Source(1):

• Scientific Literature