5-(((2S,3S)-3-(1-(3,5-dichlorophenyl)-2-hydroxyethoxy)-2-phenylpiperidin-1-yl)methyl)nicotinic acid

ID: ALA4850215

PubChem CID: 164610586

Max Phase: Preclinical

Molecular Formula: C26H26Cl2N2O4

Molecular Weight: 501.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cncc(CN2CCC[C@H](O[C@H](CO)c3cc(Cl)cc(Cl)c3)[C@@H]2c2ccccc2)c1

Standard InChI:  InChI=1S/C26H26Cl2N2O4/c27-21-10-19(11-22(28)12-21)24(16-31)34-23-7-4-8-30(25(23)18-5-2-1-3-6-18)15-17-9-20(26(32)33)14-29-13-17/h1-3,5-6,9-14,23-25,31H,4,7-8,15-16H2,(H,32,33)/t23-,24+,25-/m0/s1

Standard InChI Key:  DHFCKKJFKXZMCC-GVAUOCQISA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    4.0488  -12.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488  -13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7541  -13.4630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4594  -13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4594  -12.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7541  -11.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683  -11.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665  -13.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1621  -14.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8684  -14.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5777  -14.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5763  -13.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8694  -13.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1707  -11.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8796  -10.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5859  -11.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2943  -10.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2971   -9.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5856   -9.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8801   -9.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5851   -8.5726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0006  -11.0294    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7541  -14.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4642  -10.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666   -9.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0464  -14.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400  -14.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6328  -14.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323  -15.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450  -15.9102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493  -15.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9262  -14.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9266  -13.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2183  -14.6799    0.0000 O   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
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  7 14  1  0
 14 15  1  0
 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  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 32 33  1  0
 32 34  2  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4850215

   ---

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: 501.41

Molecular Weight (Monoisotopic): 500.1270

AlogP: 5.54

#Rotatable Bonds: 8

Polar Surface Area: 82.89

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.30

CX Basic pKa: 7.55

CX LogP: 2.15

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -0.35

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