2-(((2S,3S)-1-((1H-imidazol-2-yl)methyl)-2-phenylpiperidin-3-yl)oxy)-2-(3,5-dichlorophenyl)ethanol

ID: ALA4856290

PubChem CID: 164613010

Max Phase: Preclinical

Molecular Formula: C23H25Cl2N3O2

Molecular Weight: 446.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@@H](O[C@H]1CCCN(Cc2ncc[nH]2)[C@H]1c1ccccc1)c1cc(Cl)cc(Cl)c1

Standard InChI:  InChI=1S/C23H25Cl2N3O2/c24-18-11-17(12-19(25)13-18)21(15-29)30-20-7-4-10-28(14-22-26-8-9-27-22)23(20)16-5-2-1-3-6-16/h1-3,5-6,8-9,11-13,20-21,23,29H,4,7,10,14-15H2,(H,26,27)/t20-,21+,23-/m0/s1

Standard InChI Key:  BZXIDKITZBQUAW-XJUOHMSHSA-N

Molfile:  

 
     RDKit          2D

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    2.7198   -5.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -5.8235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -5.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -4.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -4.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393   -4.1953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -5.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8332   -6.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5395   -7.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487   -6.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2473   -5.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5404   -5.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -3.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -2.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2569   -3.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653   -2.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9681   -2.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2567   -1.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5512   -2.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562   -0.9331    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6716   -3.3899    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -6.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352   -2.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1376   -2.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -7.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -6.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -7.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -8.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6277   -7.8650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  6
  4  8  1  6
  8  9  2  0
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  7 14  1  0
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 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 17 22  1  0
  3 23  1  0
 14 24  1  6
 24 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4856290

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 446.38

Molecular Weight (Monoisotopic): 445.1324

AlogP: 5.17

#Rotatable Bonds: 7

Polar Surface Area: 61.38

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.61

CX Basic pKa: 6.60

CX LogP: 4.37

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -0.58

References

1. Hanisak J, Soriano A, Adam GC, Basso A, Bauman D, Bell D, Frank E, O'Donnell G, Tawa P, Verras A, Yu Y, Zhang L, Seganish WM..  (2021)  Discovery of the First Non-cGMP Mimetic Small Molecule Activators of cGMP-Dependent Protein Kinase 1 α (PKG1α).,  12  (8.0): [PMID:34413956] [10.1021/acsmedchemlett.1c00264]

2. Mak VW, Patel AM, Yen R, Hanisak J, Lim YH, Bao J, Zheng R, Seganish WM, Yu Y, Healy DR, Ogawa A, Ren Z, Soriano A, Ermakov GP, Beaumont M, Metwally E, Cheng AC, Verras A, Fischmann T, Zebisch M, Silvestre HL, McEwan PA, Barker J, Rearden P, Greshock TJ..  (2022)  Optimization and Mechanistic Investigations of Novel Allosteric Activators of PKG1α.,  65  (15.0): [PMID:35878399] [10.1021/acs.jmedchem.1c02109]

Source

Source(1):

• Scientific Literature