rac-(2S)-N-[(1S)-2-(5-Amino-1,3,4-oxadiazol-2-yl)-1-(4-[(2-methylpentyl)oxy]phenyl)ethyl]-2-phenylpropanamide

ID: ALA4790638

PubChem CID: 162665470

Max Phase: Preclinical

Molecular Formula: C25H32N4O3

Molecular Weight: 436.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC(C)COc1ccc([C@H](Cc2nnc(N)o2)NC(=O)[C@@H](C)c2ccccc2)cc1

Standard InChI:  InChI=1S/C25H32N4O3/c1-4-8-17(2)16-31-21-13-11-20(12-14-21)22(15-23-28-29-25(26)32-23)27-24(30)18(3)19-9-6-5-7-10-19/h5-7,9-14,17-18,22H,4,8,15-16H2,1-3H3,(H2,26,29)(H,27,30)/t17?,18-,22-/m0/s1

Standard InChI Key:  KBQRJXPPXXFCFZ-RBENRJQXSA-N

Molfile:  

 
     RDKit          2D

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    8.1712  -24.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4558  -22.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5795  -24.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2852  -23.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2144  -25.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2157  -23.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003  -23.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8009  -22.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0935  -22.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3312  -22.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425  -21.6022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425  -21.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0366  -22.1446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5857  -22.7498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1073  -20.6901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
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  6  1  1  0
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  9 13  2  0
 11 14  2  0
 14 15  1  0
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  7 19  1  6
  2 20  1  0
 20 21  1  0
 21 22  1  0
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 22 24  1  0
 24 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 27  2  0
 29 32  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA4790638

   ---

2. Parent:

   

   ALA4790638

   ---

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: 436.56

Molecular Weight (Monoisotopic): 436.2474

AlogP: 4.67

#Rotatable Bonds: 11

Polar Surface Area: 103.27

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.60

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.45

Np Likeness Score: -0.65

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]

2. Rahman MT, Decker AM, Laudermilk L, Maitra R, Ma W, Ben Hamida S, Darcq E, Kieffer BL, Jin C..  (2021)  Evaluation of Amide Bioisosteres Leading to 1,2,3-Triazole Containing Compounds as GPR88 Agonists: Design, Synthesis, and Structure-Activity Relationship Studies.,  64  (16.0): [PMID:34387471] [10.1021/acs.jmedchem.1c01075]

Source

Source(1):

• Scientific Literature