BOC-LYS(AC)-AMC::US8476255, 76

ID: ALA3647939

PubChem CID: 25264193

Max Phase: Preclinical

Molecular Formula: C26H23FN2O3S

Molecular Weight: 462.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(/C=C(/C(=O)NCc2ccc(/C=C/C(=O)NO)cc2)c2ccc(F)cc2)cc1

Standard InChI:  InChI=1S/C26H23FN2O3S/c1-33-23-13-6-19(7-14-23)16-24(21-9-11-22(27)12-10-21)26(31)28-17-20-4-2-18(3-5-20)8-15-25(30)29-32/h2-16,32H,17H2,1H3,(H,28,31)(H,29,30)/b15-8+,24-16+

Standard InChI Key:  DVHRFNSGDJIRSJ-SQTMOLFMSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024    2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4007    1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6971    0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6919   -0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9875   -1.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9802   -3.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2758   -3.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3181   -3.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2684   -5.2894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3043   -5.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3903   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0939   -0.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1931   -1.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885   -3.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834   -4.9554    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5904   -3.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  2  0
 24 13  1  0
  8 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 25  1  0
  6 32  1  0
 32 33  2  0
 33  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3647939

   (E)-2-(4-fluorophenyl)-N-[[4-[(E)-3-(hydroxyamino)-3-oxoprop-1-enyl]phenyl]methyl]-3-(4-methylsulfanylphenyl)prop-2-enamide

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: 462.55

Molecular Weight (Monoisotopic): 462.1413

AlogP: 4.92

#Rotatable Bonds: 8

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 5.07

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: -0.85

References

1.  (2013)  Histone deacetylase inhibitors, 

Source

Source(1):

• BindingDB Database