2-(4-(1,8-naphthyridin-2-yl)butyl)-5-(4-fluoro-3-(trifluoromethyl)phenyl)-1,3,4-oxadiazole

ID: ALA2153597

PubChem CID: 71449524

Max Phase: Preclinical

Molecular Formula: C21H16F4N4O

Molecular Weight: 416.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc(-c2nnc(CCCCc3ccc4cccnc4n3)o2)cc1C(F)(F)F

Standard InChI:  InChI=1S/C21H16F4N4O/c22-17-10-8-14(12-16(17)21(23,24)25)20-29-28-18(30-20)6-2-1-5-15-9-7-13-4-3-11-26-19(13)27-15/h3-4,7-12H,1-2,5-6H2

Standard InChI Key:  BHPYUJJYTNVKNQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.9559  -21.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9879  -22.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2878  -22.6571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280  -21.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5314  -21.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613  -22.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579  -22.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242  -22.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018  -21.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8016  -21.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526  -23.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4220  -22.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7847  -24.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010  -25.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700  -26.1185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763  -26.3447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1834  -25.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273  -25.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0044  -25.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449  -26.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2675  -26.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506  -25.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059  -24.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845  -24.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5860  -24.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092  -24.0889    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430  -23.4326    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876  -23.4058    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4739  -25.5216    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 14 15  1  0
 16 17  1  0
  1  2  2  0
  7  8  2  0
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  8  9  1  0
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  4  1  1  0
  9 10  2  0
 20 21  2  0
 10  5  1  0
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  8 12  1  0
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  2  3  1  0
 24 25  2  0
 25 20  1  0
 18 20  1  0
 12 11  1  0
 24 26  1  0
  5  6  1  0
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  3  6  2  0
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 13 14  1  0
 23 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2153597

   2-[4-Fluoro-3-(trifluoromethyl)phenyl]-5-[4-(1,8-naphthyridin-2-yl)butyl]-1,3,4-oxadiazole

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: 416.38

Molecular Weight (Monoisotopic): 416.1260

AlogP: 5.40

#Rotatable Bonds: 6

Polar Surface Area: 64.70

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.16

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -1.45

References

1. Bhuniya D, Umrani D, Dave B, Salunke D, Kukreja G, Gundu J, Naykodi M, Shaikh NS, Shitole P, Kurhade S, De S, Majumdar S, Reddy SB, Tambe S, Shejul Y, Chugh A, Palle VP, Mookhtiar KA, Cully D, Vacca J, Chakravarty PK, Nargund RP, Wright SD, Graziano MP, Singh SB, Roy S, Cai TQ..  (2011)  Discovery of a potent and selective small molecule hGPR91 antagonist.,  21  (12): [PMID:21571530] [10.1016/j.bmcl.2011.04.091]

Source

Source(1):

• Scientific Literature