N-(2,4-dimethylphenyl)sulfonyl-2-(2-naphthyloxy)acetamide

ID: ALA4534834

Cas Number: 868145-09-9

PubChem CID: 2145430

Max Phase: Preclinical

Molecular Formula: C20H19NO4S

Molecular Weight: 369.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NC(=O)COc2ccc3ccccc3c2)c(C)c1

Standard InChI:  InChI=1S/C20H19NO4S/c1-14-7-10-19(15(2)11-14)26(23,24)21-20(22)13-25-18-9-8-16-5-3-4-6-17(16)12-18/h3-12H,13H2,1-2H3,(H,21,22)

Standard InChI Key:  KCRXXSQZEZOCFM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   20.5536  -27.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9663  -28.2220    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.3747  -27.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8449  -28.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5526  -28.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5526  -27.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2603  -28.6347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6758  -28.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6707  -29.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3793  -29.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0925  -29.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0925  -28.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3833  -28.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9610  -29.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7994  -29.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1372  -28.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4295  -28.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7224  -28.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7274  -29.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4317  -29.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0147  -29.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0192  -28.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3159  -28.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6077  -28.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6072  -29.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3110  -29.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  2  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  9 14  1  0
 11 15  1  0
  4 16  1  0
 16 17  1  0
 17 18  2  0
 18 22  1  0
 21 19  1  0
 19 20  2  0
 20 17  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534834

   N-((2,4-dimethylphenyl)sulfonyl)-2-(naphthalen-2-yloxy)acetamide

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: 369.44

Molecular Weight (Monoisotopic): 369.1035

AlogP: 3.34

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.93

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -1.31

References

1. Wang P, Luchowska-Stańska U, van Basten B, Chen H, Liu Z, Wiejak J, Whelan P, Morgan D, Lochhead E, Barker G, Rehmann H, Yarwood SJ, Zhou J..  (2020)  Synthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators.,  63  (10): [PMID:32340447] [10.1021/acs.jmedchem.9b02094]

2. Shao H, Mohamed H, Boulton S, Huang J, Wang P, Chen H, Zhou J, Luchowska-Stańska U, Jentsch NG, Armstrong AL, Magolan J, Yarwood S, Melacini G..  (2020)  Mechanism of Action of an EPAC1-Selective Competitive Partial Agonist.,  63  (9): [PMID:32297742] [10.1021/acs.jmedchem.9b02151]

Source

Source(1):

• Scientific Literature