3-((2S,3S)-3-((S)-1-(3,5-Dichlorophenyl)-2-hydroxyethoxy)-2-phenylpiperidin-1-yl)methyl)bicyclo[1.1.1]pentane-1-carboxylic Acid

ID: ALA5171400

PubChem CID: 168269017

Max Phase: Preclinical

Molecular Formula: C26H29Cl2NO4

Molecular Weight: 490.43

Names and Identifiers

Canonical SMILES:  O=C(O)C12CC(CN3CCC[C@H](O[C@H](CO)c4cc(Cl)cc(Cl)c4)[C@@H]3c3ccccc3)(C1)C2

Standard InChI:  InChI=1S/C26H29Cl2NO4/c27-19-9-18(10-20(28)11-19)22(12-30)33-21-7-4-8-29(23(21)17-5-2-1-3-6-17)16-25-13-26(14-25,15-25)24(31)32/h1-3,5-6,9-11,21-23,30H,4,7-8,12-16H2,(H,31,32)/t21-,22+,23-,25?,26?/m0/s1

Standard InChI Key:  NUFMMTFQNSFHJT-LTFOVQEUSA-N

Molfile:  

 
     RDKit          2D

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    2.2912    4.0041    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2912    3.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 26  2  0
 27 18  1  0
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 10 29  1  0
  8 30  1  6
 30 31  1  0
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 23 33  1  0
 33 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5171400

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 490.43

Molecular Weight (Monoisotopic): 489.1474

AlogP: 5.50

#Rotatable Bonds: 8

Polar Surface Area: 70.00

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.84

CX Basic pKa: 9.01

CX LogP: 2.44

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: 0.06

References

1. 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