4-(3-((2-bromophenyl)amino)-3-oxoprop-1-en-1-yl)-2-methoxyphenyl butane-1-sulfonate

ID: ALA5203215

PubChem CID: 168292774

Max Phase: Preclinical

Molecular Formula: C20H22BrNO5S

Molecular Weight: 468.37

Names and Identifiers

Canonical SMILES:  CCCCS(=O)(=O)Oc1ccc(/C=C/C(=O)Nc2ccccc2Br)cc1OC

Standard InChI:  InChI=1S/C20H22BrNO5S/c1-3-4-13-28(24,25)27-18-11-9-15(14-19(18)26-2)10-12-20(23)22-17-8-6-5-7-16(17)21/h5-12,14H,3-4,13H2,1-2H3,(H,22,23)/b12-10+

Standard InChI Key:  KQDSFCMALOUPPC-ZRDIBKRKSA-N

Molfile:  

 
     RDKit          2D

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    0.3574    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592   -0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    0.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010    1.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592   -1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4986   -0.4123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9279   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9119    0.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    0.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6451    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6469    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303    1.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6451   -0.4126    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  5 12  1  0
 12 13  1  0
  4 14  1  0
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 18 19  1  0
 15 20  2  0
 15 21  2  0
 10 22  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 22 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203215

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 468.37

Molecular Weight (Monoisotopic): 467.0402

AlogP: 4.62

#Rotatable Bonds: 9

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.23

CX Basic pKa: ┄

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.74

References

1. Yang YS, Wang B, Zhou KM, Liu J, Jiao QC, Qin P..  (2022)  Discovery of derivatives from Spartina alterniflora-sourced moiety as xanthine oxidase inhibitors to lower uric acid.,  73  [PMID:35902063] [10.1016/j.bmcl.2022.128907]

Source

Source(1):

• Scientific Literature