2-(1-Adamantyl)ethyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate

ID: ALA3746867

PubChem CID: 127038653

Max Phase: Preclinical

Molecular Formula: C20H28N2O5

Molecular Weight: 376.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OCCC12CC3CC(CC(C3)C1)C2)c1cc(N(O)C2CCCO2)on1

Standard InChI:  InChI=1S/C20H28N2O5/c23-19(16-9-18(27-21-16)22(24)17-2-1-4-25-17)26-5-3-20-10-13-6-14(11-20)8-15(7-13)12-20/h9,13-15,17,24H,1-8,10-12H2

Standard InChI Key:  RNHOAJFMWVCHFT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.2700    6.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7646    6.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3472    5.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    4.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423    8.1672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9650    9.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0427    8.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9309    9.3279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3461    8.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3109    7.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8738    6.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    4.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    5.4447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    3.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300    2.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5893   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839    1.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  1  0
  6  8  1  0
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  9 10  1  0
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 11 12  1  0
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  1 13  1  0
 13 14  2  0
 13 15  1  0
 16 17  1  0
 16 18  1  0
 17 19  1  0
 18 20  1  0
 19 21  1  0
 20 21  1  0
 22 23  1  0
 18 22  1  0
 17 24  1  0
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 21 26  1  0
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 27 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3746867

   ---

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: 376.45

Molecular Weight (Monoisotopic): 376.1998

AlogP: 3.77

#Rotatable Bonds: 6

Polar Surface Area: 85.03

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.31

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: 3.72

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -0.44

References

1. Averina EB, Vasilenko DA, Gracheva YA, Grishin YK, Radchenko EV, Burmistrov VV, Butov GM, Neganova ME, Serkova TP, Redkozubova OM, Shevtsova EF, Milaeva ER, Kuznetsova TS, Zefirov NS..  (2016)  Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents.,  24  (4): [PMID:26753816] [10.1016/j.bmc.2015.12.040]

Source

Source(1):

• Scientific Literature