2-(2,4-Difluorophenyl)-1-(4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)piperidin-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

ID: ALA3735849

PubChem CID: 127034970

Max Phase: Preclinical

Molecular Formula: C22H22F2N6O3

Molecular Weight: 456.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC(CN1CCC(c2nnc(-c3ccco3)o2)CC1)(Cn1cncn1)c1ccc(F)cc1F

Standard InChI:  InChI=1S/C22H22F2N6O3/c23-16-3-4-17(18(24)10-16)22(31,12-30-14-25-13-26-30)11-29-7-5-15(6-8-29)20-27-28-21(33-20)19-2-1-9-32-19/h1-4,9-10,13-15,31H,5-8,11-12H2

Standard InChI Key:  XDQBVQOQXXCZLQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    1.2948   -3.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -5.2541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -6.1147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -7.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -7.5401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5067   -6.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7390    2.9810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067    3.2905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1939   -3.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938   -2.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4957   -0.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8977   -0.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5357   -0.1598    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923   -4.2068    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4469    1.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5110    2.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8282    2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5529    0.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0654    0.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
  1  5  1  0
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  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
  4 14  1  0
 10 11  1  0
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 17 18  2  0
 18 19  1  0
 19 15  1  0
  2 20  1  0
  2 21  1  0
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 26 21  1  0
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 22 28  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 29  2  0
 18 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735849

   ---

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: 456.45

Molecular Weight (Monoisotopic): 456.1721

AlogP: 2.97

#Rotatable Bonds: 7

Polar Surface Area: 106.24

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.85

CX Basic pKa: 7.86

CX LogP: 1.50

CX LogD: 0.90

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -1.57

References

1. He X, Jiang Y, Zhang Y, Wu S, Dong G, Liu N, Liu Y, Yao J, Miao Z, Wang Y, Zhang W, Sheng C.  (2015)  Discovery of highly potent triazoleantifungal agents with piperidine-oxadiazole side chains,  6  (4): [10.1039/C4MD00505H]

Source

Source(1):

• Scientific Literature