4-(1-(4-(3-(hydroxyamino)-3-oxoprop-1-enyl)benzamido)propan-2-yloxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

ID: ALA4549965

PubChem CID: 101882458

Max Phase: Preclinical

Molecular Formula: C21H20N4O8S

Molecular Weight: 488.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(CNC(=O)c1ccc(/C=C/C(=O)NO)cc1)Oc1no[n+]([O-])c1S(=O)(=O)c1ccccc1

Standard InChI:  InChI=1S/C21H20N4O8S/c1-14(13-22-19(27)16-10-7-15(8-11-16)9-12-18(26)23-28)32-20-21(25(29)33-24-20)34(30,31)17-5-3-2-4-6-17/h2-12,14,28H,13H2,1H3,(H,22,27)(H,23,26)/b12-9+

Standard InChI Key:  VDLUORLDWZKKDW-FMIVXFBMSA-N

Molfile:  

 
     RDKit          2D

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    6.5476  -19.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7054  -19.8395    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.3260  -19.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9816  -21.2694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6595  -21.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0235  -20.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7873  -20.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5939  -20.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0202  -18.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8356  -18.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6603  -17.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1939  -19.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0084  -19.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4646  -18.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1004  -17.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2870  -17.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2800  -18.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6410  -19.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4564  -19.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8174  -20.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9108  -18.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6328  -20.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
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  6  7  2  0
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  8  4  2  0
  8  2  1  0
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  9 10  2  0
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  7 15  1  0
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  4 17  1  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 26 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 32 34  1  0
M  CHG  2   4   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4549965

   N-[2-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]propyl]-4-[(E)-3-(hydroxyamino)-3-oxoprop-1-enyl]benzamide

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: 488.48

Molecular Weight (Monoisotopic): 488.1002

AlogP: 0.86

#Rotatable Bonds: 9

Polar Surface Area: 174.77

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: 0.43

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.17

Np Likeness Score: -0.78

References

1. Sangwan R, Rajan R, Mandal PK..  (2018)  HDAC as onco target: Reviewing the synthetic approaches with SAR study of their inhibitors.,  158  [PMID:30245394] [10.1016/j.ejmech.2018.08.073]

2. Bass AKA, El-Zoghbi MS, Nageeb EM, Mohamed MFA, Badr M, Abuo-Rahma GEA..  (2021)  Comprehensive review for anticancer hybridized multitargeting HDAC inhibitors.,  209  [PMID:33077264] [10.1016/j.ejmech.2020.112904]

Source

Source(1):

• Scientific Literature