(2S)-N-[(1R)-1-(4-Butoxyphenyl)-2-hydroxyethyl]-2-phenylpropanamide

ID: ALA4776381

PubChem CID: 162643654

Max Phase: Preclinical

Molecular Formula: C21H27NO3

Molecular Weight: 341.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc([C@H](CO)NC(=O)[C@@H](C)c2ccccc2)cc1

Standard InChI:  InChI=1S/C21H27NO3/c1-3-4-14-25-19-12-10-18(11-13-19)20(15-23)22-21(24)16(2)17-8-6-5-7-9-17/h5-13,16,20,23H,3-4,14-15H2,1-2H3,(H,22,24)/t16-,20-/m0/s1

Standard InChI Key:  NDYGPFJMJJINIY-JXFKEZNVSA-N

Molfile:  

 
     RDKit          2D

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   21.2084  -16.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2073  -17.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9153  -17.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6250  -17.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6221  -16.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9135  -16.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3283  -16.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0375  -16.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7437  -16.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4530  -16.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1591  -16.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4560  -17.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7406  -15.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8644  -16.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5701  -16.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5674  -15.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8532  -14.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1504  -15.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3252  -15.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6160  -14.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4992  -17.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7918  -17.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7925  -16.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5005  -16.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5012  -15.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
  9 13  2  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 11  1  0
  7 19  1  6
 19 20  1  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776381

   ---

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: 341.45

Molecular Weight (Monoisotopic): 341.1991

AlogP: 3.82

#Rotatable Bonds: 9

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.08

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -0.56

References

1. Rahman MT,Decker AM,Langston TL,Mathews KM,Laudermilk L,Maitra R,Ma W,Darcq E,Kieffer BL,Jin C.  (2020)  Design, Synthesis, and Structure-Activity Relationship Studies of (4-Alkoxyphenyl)glycinamides and Bioisosteric 1,3,4-Oxadiazoles as GPR88 Agonists.,  63  (23): [PMID:33205975] [10.1021/acs.jmedchem.0c01581]

Source

Source(1):

• Scientific Literature