3-(((2S,3S)-3-((3,5-dichlorobenzyl)oxy)-2-phenylpiperidin-1-yl)methyl)-4-methoxybenzoic acid

ID: ALA4876308

PubChem CID: 164628239

Max Phase: Preclinical

Molecular Formula: C27H27Cl2NO4

Molecular Weight: 500.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)O)cc1CN1CCC[C@H](OCc2cc(Cl)cc(Cl)c2)[C@@H]1c1ccccc1

Standard InChI:  InChI=1S/C27H27Cl2NO4/c1-33-24-10-9-20(27(31)32)14-21(24)16-30-11-5-8-25(26(30)19-6-3-2-4-7-19)34-17-18-12-22(28)15-23(29)13-18/h2-4,6-7,9-10,12-15,25-26H,5,8,11,16-17H2,1H3,(H,31,32)/t25-,26-/m0/s1

Standard InChI Key:  KOSSJLXCGDNXRR-UIOOFZCWSA-N

Molfile:  

 
     RDKit          2D

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   27.6689  -11.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3742  -11.6388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   29.7823  -12.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.1978  -12.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.2053   -6.7484    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.6207   -9.2052    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.3742  -12.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6665  -12.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9601  -12.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2529  -12.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2524  -13.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9651  -14.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6694  -13.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5435  -12.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5439  -11.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8356  -12.8573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3787  -14.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3817  -14.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
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 30 32  2  0
 26 30  1  0
 29 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876308

   ---

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: 500.42

Molecular Weight (Monoisotopic): 499.1317

AlogP: 6.62

#Rotatable Bonds: 8

Polar Surface Area: 59.00

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.87

CX Basic pKa: 7.93

CX LogP: 3.87

CX LogD: 3.78

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: -0.49

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]

Source

Source(1):

• Scientific Literature