4-(((2S,3S)-3-(1-(3,5-dichlorophenyl)-2-hydroxyethoxy)-2-phenylpiperidin-1-yl)methyl)benzoic acid

ID: ALA4860278

PubChem CID: 164618103

Max Phase: Preclinical

Molecular Formula: C27H27Cl2NO4

Molecular Weight: 500.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(CN2CCC[C@H](O[C@H](CO)c3cc(Cl)cc(Cl)c3)[C@@H]2c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H27Cl2NO4/c28-22-13-21(14-23(29)15-22)25(17-31)34-24-7-4-12-30(26(24)19-5-2-1-3-6-19)16-18-8-10-20(11-9-18)27(32)33/h1-3,5-6,8-11,13-15,24-26,31H,4,7,12,16-17H2,(H,32,33)/t24-,25+,26-/m0/s1

Standard InChI Key:  IGWIUKYUKCCQNT-NXCFDTQHSA-N

Molfile:  

 
     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA4860278

   ---

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: 6.15

#Rotatable Bonds: 8

Polar Surface Area: 70.00

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.69

CX Basic pKa: 8.44

CX LogP: 3.35

CX LogD: 3.32

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: -0.26

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