4-((2S,3S)-3-((S)-1-(3,5-Dichlorophenyl)-2-hydroxyethoxy)-2-phenylpiperidine-1-carbonyl)-3-methylbenzoic Acid

ID: ALA5170219

PubChem CID: 168271054

Max Phase: Preclinical

Molecular Formula: C28H27Cl2NO5

Molecular Weight: 528.43

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)O)ccc1C(=O)N1CCC[C@H](O[C@H](CO)c2cc(Cl)cc(Cl)c2)[C@@H]1c1ccccc1

Standard InChI:  InChI=1S/C28H27Cl2NO5/c1-17-12-19(28(34)35)9-10-23(17)27(33)31-11-5-8-24(26(31)18-6-3-2-4-7-18)36-25(16-32)20-13-21(29)15-22(30)14-20/h2-4,6-7,9-10,12-15,24-26,32H,5,8,11,16H2,1H3,(H,34,35)/t24-,25+,26-/m0/s1

Standard InChI Key:  GRDBZKBQOMABTH-NXCFDTQHSA-N

Molfile:  

 
     RDKit          2D

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    1.7870    2.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2157    2.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301    1.6488    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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 34 36  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5170219

   ---

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: 528.43

Molecular Weight (Monoisotopic): 527.1266

AlogP: 6.10

#Rotatable Bonds: 7

Polar Surface Area: 87.07

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 5.95

CX LogD: 2.66

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.39

Np Likeness Score: -0.40

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