N-[{3-(3-trifluoromethyl-4-fluorophenyl)isoxazol-5-yl}methyl]-4-([1,8]naphthyridin-2-yl)butyramide

ID: ALA2153581

Cas Number: 1314796-31-0

PubChem CID: 53358901

Product Number: N609333, Order Now?

Max Phase: Preclinical

Molecular Formula: C23H18F4N4O2

Molecular Weight: 458.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCc1ccc2cccnc2n1)NCc1cc(-c2ccc(F)c(C(F)(F)F)c2)no1

Standard InChI:  InChI=1S/C23H18F4N4O2/c24-19-9-7-15(11-18(19)23(25,26)27)20-12-17(33-31-20)13-29-21(32)5-1-4-16-8-6-14-3-2-10-28-22(14)30-16/h2-3,6-12H,1,4-5,13H2,(H,29,32)

Standard InChI Key:  SWKGPCNQBPGWNX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.2935  -18.1944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8678  -18.1374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2612  -19.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9376  -19.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4223  -14.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3903  -15.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0912  -15.5656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1511  -13.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8486  -14.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8146  -15.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5188  -15.6201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2534  -15.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2800  -14.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.7405  -20.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2124  -19.8791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7122  -19.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1589  -21.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7515  -21.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1691  -22.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9948  -22.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4013  -21.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9817  -21.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4138  -23.3941    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.2262  -21.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6465  -22.6589    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.6306  -21.2323    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.0479  -21.9480    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 10  9  2  0
 16 18  1  0
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  9  6  1  0
  4  5  1  0
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 21 22  1  0
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  6  7  2  0
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  2  4  1  0
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  7  8  1  0
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 27 30  1  0
 15 10  1  0
 30 31  1  0
 13 17  1  0
 30 32  1  0
  8 11  2  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2153581

   N-[[3-[4-fluoro-3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]methyl]-4-(1,8-naphthyridin-2-yl)butanamide

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: 458.42

Molecular Weight (Monoisotopic): 458.1366

AlogP: 5.08

#Rotatable Bonds: 7

Polar Surface Area: 80.91

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.38

CX Basic pKa: 0.57

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.39

Np Likeness Score: -1.58

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