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

ID: ALA4568722

PubChem CID: 101882456

Max Phase: Preclinical

Molecular Formula: C21H20N4O8S

Molecular Weight: 488.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(C(=O)NCCCOc2no[n+]([O-])c2S(=O)(=O)c2ccccc2)cc1)NO

Standard InChI:  InChI=1S/C21H20N4O8S/c26-18(23-28)12-9-15-7-10-16(11-8-15)19(27)22-13-4-14-32-20-21(25(29)33-24-20)34(30,31)17-5-2-1-3-6-17/h1-3,5-12,28H,4,13-14H2,(H,22,27)(H,23,26)/b12-9+

Standard InChI Key:  HHDQWMHNXRESPD-FMIVXFBMSA-N

Molfile:  

 
     RDKit          2D

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    6.2670  -11.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4247  -12.6045    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0454  -12.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7009  -14.0343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3788  -14.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3132  -13.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1982  -12.5397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7396  -11.2927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5549  -11.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0103  -10.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9149  -12.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8262  -10.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2814  -10.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9215   -9.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1017   -9.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6502   -9.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3759   -8.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1913   -8.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6457   -8.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4612   -8.0643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2848   -7.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9156   -7.3851    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
  5  6  1  0
  6  7  2  0
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  8  2  1  0
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  7 15  1  0
 15 16  1  0
  4 17  1  0
 16 18  1  0
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 20 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:

   

   ALA4568722

   N-[3-[[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: 10

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: 0.07

CX LogD: 0.07

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.12

Np Likeness Score: -0.88

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