5-Hydroxy-N-(3-(5-p-tolyl-1,3,4-oxadiazol-2-yl)phenyl)pentanamide

ID: ALA3287957

PubChem CID: 90681032

Max Phase: Preclinical

Molecular Formula: C20H21N3O3

Molecular Weight: 351.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2nnc(-c3cccc(NC(=O)CCCCO)c3)o2)cc1

Standard InChI:  InChI=1S/C20H21N3O3/c1-14-8-10-15(11-9-14)19-22-23-20(26-19)16-5-4-6-17(13-16)21-18(25)7-2-3-12-24/h4-6,8-11,13,24H,2-3,7,12H2,1H3,(H,21,25)

Standard InChI Key:  ZQSZVNJWWRJXNQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.5777   -2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5765   -3.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2913   -3.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0078   -3.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0050   -2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2895   -2.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8631   -2.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7228   -3.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6929   -4.5481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4689   -4.8279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9749   -4.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5113   -3.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7995   -4.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1865   -4.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0102   -4.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4461   -4.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0520   -3.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2296   -3.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3995   -5.6834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2241   -5.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6134   -6.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6595   -5.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4380   -6.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8273   -7.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6518   -7.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0411   -7.9452    0.0000 O   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
  1  7  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3287957

   5-hydroxy-N-[3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]pentanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

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: 3.81

#Rotatable Bonds: 7

Polar Surface Area: 88.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -1.16

References

1. Liao BR, He HB, Yang LL, Gao LX, Chang L, Tang J, Li JY, Li J, Yang F..  (2014)  Synthesis and structure-activity relationship of non-phosphorus-based fructose-1,6-bisphosphatase inhibitors: 2,5-Diphenyl-1,3,4-oxadiazoles.,  83  [PMID:24946215] [10.1016/j.ejmech.2014.06.011]

2. Kerru N, Singh-Pillay A, Awolade P, Singh P..  (2018)  Current anti-diabetic agents and their molecular targets: A review.,  152  [PMID:29751237] [10.1016/j.ejmech.2018.04.061]

Source

Source(1):

• Scientific Literature