tert-butyl N-[4-[3-[2-[3-(hydroxycarbamoyl)isoxazol-5-yl]ethylcarbamoyl]isoxazol-5-yl]phenyl]carbamate

ID: ALA4554511

PubChem CID: 126649182

Max Phase: Preclinical

Molecular Formula: C21H23N5O7

Molecular Weight: 457.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)Nc1ccc(-c2cc(C(=O)NCCc3cc(C(=O)NO)no3)no2)cc1

Standard InChI:  InChI=1S/C21H23N5O7/c1-21(2,3)31-20(29)23-13-6-4-12(5-7-13)17-11-16(26-33-17)18(27)22-9-8-14-10-15(25-32-14)19(28)24-30/h4-7,10-11,30H,8-9H2,1-3H3,(H,22,27)(H,23,29)(H,24,28)

Standard InChI Key:  RHGZKRZZDBBXMP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    8.5062   -9.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8450   -8.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949   -7.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9134   -7.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1674   -8.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3249   -7.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9134   -6.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1436   -7.2231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5509   -6.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3696   -6.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7810   -5.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4459   -5.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0546   -4.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7616   -4.9222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5928   -5.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0546   -3.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3472   -3.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7621   -3.2851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7621   -2.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0537   -8.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8415   -9.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0533   -9.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4737   -9.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6861   -8.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -8.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825   -9.5579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706  -10.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835  -10.5611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716  -11.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803  -11.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0509  -11.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2597  -12.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0499  -10.9285    0.0000 O   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  2  0
  5  1  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 20  2  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 20 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 27 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554511

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 457.44

Molecular Weight (Monoisotopic): 457.1597

AlogP: 2.77

#Rotatable Bonds: 7

Polar Surface Area: 168.82

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.08

CX Basic pKa: ┄

CX LogP: 1.58

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -1.41

References

1. Shen S, Hadley M, Ustinova K, Pavlicek J, Knox T, Noonepalle S, Tavares MT, Zimprich CA, Zhang G, Robers MB, Bařinka C, Kozikowski AP, Villagra A..  (2019)  Discovery of a New Isoxazole-3-hydroxamate-Based Histone Deacetylase 6 Inhibitor SS-208 with Antitumor Activity in Syngeneic Melanoma Mouse Models.,  62  (18): [PMID:31414801] [10.1021/acs.jmedchem.9b00946]

Source

Source(1):

• Scientific Literature