2-{4-[5-(3-Chloro-4-trifluoromethoxyphenyl)-[1,3,4]oxadiazol-2-yl]butyl}-[1,8]naphthyridine

ID: ALA2153595

PubChem CID: 71449523

Max Phase: Preclinical

Molecular Formula: C21H16ClF3N4O2

Molecular Weight: 448.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)Oc1ccc(-c2nnc(CCCCc3ccc4cccnc4n3)o2)cc1Cl

Standard InChI:  InChI=1S/C21H16ClF3N4O2/c22-16-12-14(8-10-17(16)31-21(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:  SCIJCWVEPLKBGV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -6.0155  -14.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3076  -14.6026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2421  -18.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251  -17.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805  -16.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593  -16.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4482  -17.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899  -18.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7130  -18.1293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084  -18.8943    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723  -18.7417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5605  -16.0740    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
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 27 30  1  0
  6  7  1  0
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2153595

   2-[3-Chloro-4-(trifluoromethoxy)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: 448.83

Molecular Weight (Monoisotopic): 448.0914

AlogP: 5.80

#Rotatable Bonds: 7

Polar Surface Area: 73.93

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.16

CX LogP: 5.44

CX LogD: 5.44

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -1.37

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]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data