3-(4-(3-(Naphthalen-2-yl)-1,2,4-oxadiazol-5-yl)piperidin-1-yl)propanoic acid

ID: ALA4522124

PubChem CID: 155542847

Max Phase: Preclinical

Molecular Formula: C20H21N3O3

Molecular Weight: 351.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CCN1CCC(c2nc(-c3ccc4ccccc4c3)no2)CC1

Standard InChI:  InChI=1S/C20H21N3O3/c24-18(25)9-12-23-10-7-15(8-11-23)20-21-19(22-26-20)17-6-5-14-3-1-2-4-16(14)13-17/h1-6,13,15H,7-12H2,(H,24,25)

Standard InChI Key:  DCZJTSMCCLMUNU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   28.3735   -9.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1551  -10.2155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6250   -9.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1316   -8.8922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3609   -9.1612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4421   -9.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7205  -10.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9709  -10.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1739  -11.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8233  -11.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8580  -10.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6716  -10.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0722   -9.5144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6531   -8.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8333   -8.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4170  -11.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3200  -10.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5702  -10.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9168  -10.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0181  -11.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7680  -11.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8893   -9.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2888   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1059   -8.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5053   -8.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5235   -9.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  1  7  1  0
  7  8  2  0
  8 17  1  0
 16  9  1  0
  9 10  2  0
 10  7  1  0
  6 11  1  0
  6 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522124

   ---

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: 351.41

Molecular Weight (Monoisotopic): 351.1583

AlogP: 3.54

#Rotatable Bonds: 5

Polar Surface Area: 79.46

Molecular Species: ZWITTERION

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.69

CX Basic pKa: 8.85

CX LogP: 0.58

CX LogD: 0.57

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -1.46

References

1. Festa C, Finamore C, Marchianò S, Di Leva FS, Carino A, Monti MC, Del Gaudio F, Ceccacci S, Limongelli V, Zampella A, Fiorucci S, De Marino S..  (2019)  Investigation around the Oxadiazole Core in the Discovery of a New Chemotype of Potent and Selective FXR Antagonists.,  10  (4): [PMID:30996787] [10.1021/acsmedchemlett.8b00534]

Source

Source(1):

• Scientific Literature