methyl 4-(2-((1S,5R,6s)-6-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetamido)-3-aza-bicyclo[3.1.0]hexan-3-yl)ethyl)benzoate

ID: ALA249204

PubChem CID: 10344314

Max Phase: Preclinical

Molecular Formula: C28H34N2O4

Molecular Weight: 462.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(CCN2C[C@@H]3[C@H](C2)[C@H]3NC(=O)C(O)(c2ccccc2)C2CCCC2)cc1

Standard InChI:  InChI=1S/C28H34N2O4/c1-34-26(31)20-13-11-19(12-14-20)15-16-30-17-23-24(18-30)25(23)29-27(32)28(33,22-9-5-6-10-22)21-7-3-2-4-8-21/h2-4,7-8,11-14,22-25,33H,5-6,9-10,15-18H2,1H3,(H,29,32)/t23-,24+,25+,28?

Standard InChI Key:  YGHIXHGNVUQBRE-BKWJHWGASA-N

Molfile:  

     RDKit          2D

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    6.2480  -25.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6606  -26.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4854  -26.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3982  -26.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0107  -25.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8356  -25.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2540  -26.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0781  -26.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3069  -25.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7312  -26.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 17  1  0
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  9 21  1  0
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  4  1  1  0
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 12 13  1  0
 27 28  2  0
  1  2  1  0
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 29 30  2  0
  2  3  1  0
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 14 15  1  0
 31 32  2  0
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  6  7  1  6
 15 16  2  0
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 33 35  2  0
 30 33  1  0
  3  5  1  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA249204

   methyl 4-(2-((1S,5R,6s)-6-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetamido)-3-aza-bicyclo[3.1.0]hexan-3-yl)ethyl)benzoate

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: 462.59

Molecular Weight (Monoisotopic): 462.2519

AlogP: 3.14

#Rotatable Bonds: 8

Polar Surface Area: 78.87

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.98

CX Basic pKa: 8.64

CX LogP: 3.71

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.59

Np Likeness Score: -0.30

References

1. Kumar N, Kaur K, Aeron S, Dharmarajan S, Silamkoti AD, Mehta A, Gupta S, Chugh A, Gupta JB, Salman M, Palle VP, Cliffe IA..  (2007)  Synthesis and optimization of novel and selective muscarinic M(3) receptor antagonists.,  17  (18): [PMID:17629699] [10.1016/j.bmcl.2007.06.081]

Source

Source(1):

• Scientific Literature