3-(i-propoxycarbonyl)-1-adamantyl 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazole-3-carboxylate

ID: ALA3747650

PubChem CID: 127038654

Max Phase: Preclinical

Molecular Formula: C22H30N2O7

Molecular Weight: 434.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)C12CC3CC(CC(OC(=O)c4cc(N(O)C5CCCO5)on4)(C3)C1)C2

Standard InChI:  InChI=1S/C22H30N2O7/c1-13(2)29-20(26)21-8-14-6-15(9-21)11-22(10-14,12-21)30-19(25)16-7-18(31-23-16)24(27)17-4-3-5-28-17/h7,13-15,17,27H,3-6,8-12H2,1-2H3

Standard InChI Key:  JDEOBSVVIRKKQI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    3.9110    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5567    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0406    1.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904    0.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9609   -0.6251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0913    2.6166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7710    3.7731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5444    2.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6826    3.1982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9460    2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5676    0.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0702    0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4316    0.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653    1.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9101   -1.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -1.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600   -1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -1.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4900   -0.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -0.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000   -2.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -2.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400   -1.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722    1.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    1.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266    3.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    4.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    4.0205    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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  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
 21 25  1  0
 25 23  1  0
 23 24  1  0
 21 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 17 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3747650

   ---

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: 434.49

Molecular Weight (Monoisotopic): 434.2053

AlogP: 3.45

#Rotatable Bonds: 6

Polar Surface Area: 111.33

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.31

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.51

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -0.30

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