4-(1-Adamantyl)benzyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate

ID: ALA3746445

PubChem CID: 127038655

Max Phase: Preclinical

Molecular Formula: C25H30N2O5

Molecular Weight: 438.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OCc1ccc(C23CC4CC(CC(C4)C2)C3)cc1)c1cc(N(O)C2CCCO2)on1

Standard InChI:  InChI=1S/C25H30N2O5/c28-24(21-11-23(32-26-21)27(29)22-2-1-7-30-22)31-15-16-3-5-20(6-4-16)25-12-17-8-18(13-25)10-19(9-17)14-25/h3-6,11,17-19,22,29H,1-2,7-10,12-15H2

Standard InChI Key:  ZPBVBAGLRHZELG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.0318    7.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7483    8.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598    8.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6233    7.4476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7699    9.7163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9391    9.4462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3317   11.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   12.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3765   13.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427   13.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1490    4.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    2.1909    1.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9978    0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861    0.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    2.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163    3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0002    2.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 13  1  0
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 31 26  1  0
 29 32  1  0
 32 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3746445

   ---

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: 438.52

Molecular Weight (Monoisotopic): 438.2155

AlogP: 4.83

#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: 4.88

CX LogD: 5.08

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: -0.51

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