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

ID: ALA3746662

PubChem CID: 102336052

Max Phase: Preclinical

Molecular Formula: C19H26N2O5

Molecular Weight: 362.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OCC12CC3CC(CC(C3)C1)C2)c1cc(N(O)C2CCCO2)on1

Standard InChI:  InChI=1S/C19H26N2O5/c22-18(15-7-17(26-20-15)21(23)16-2-1-3-24-16)25-11-19-8-12-4-13(9-19)6-14(5-12)10-19/h7,12-14,16,23H,1-6,8-11H2

Standard InChI Key:  ATRRNMVKSDCRIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
    0.9852    0.2541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953   -0.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0132    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8712   -0.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -2.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -1.5498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -0.8769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9909    0.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0923   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5696   -2.3637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8478   -3.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5319   -4.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4404   -3.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966    0.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    2.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
  6 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  2  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 13 25  1  0
 25 26  2  0
 25 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3746662

   1-Adamantylmethyl 5-[hydroxy(oxolan-2-yl)amino]-1,2-oxazole-3-carboxylate

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: 362.43

Molecular Weight (Monoisotopic): 362.1842

AlogP: 3.38

#Rotatable Bonds: 5

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: 3.23

CX LogD: 3.43

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.38

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