US8476255, 84

ID: ALA3647941

PubChem CID: 59475052

Max Phase: Preclinical

Molecular Formula: C23H27FN2O3S

Molecular Weight: 430.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H27FN2O3S/c1-30-20-13-7-17(8-14-20)16-21(18-9-11-19(24)12-10-18)23(28)25-15-5-3-2-4-6-22(27)26-29/h7-14,16,29H,2-6,15H2,1H3,(H,25,28)(H,26,27)/b21-16+

Standard InChI Key:  UWOLQCFZNNRZKN-LTGZKZEYSA-N

Molfile:  

     RDKit          2D

 30 31  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    1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1982    1.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2377    0.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1978    2.9978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4969    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4966    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7957    6.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7953    7.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0944    8.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0941    9.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3932   10.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4327    9.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3928   12.0073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   12.6082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977   -0.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002   -1.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6030   -3.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -4.9554    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2011   -3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1982   -1.5029    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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 22  1  0
  6 29  1  0
 29 30  2  0
 30  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3647941

   7-[[(E)-2-(4-fluorophenyl)-3-(4-methylsulfanylphenyl)prop-2-enoyl]amino]-N-hydroxyheptanamide

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: 430.55

Molecular Weight (Monoisotopic): 430.1726

AlogP: 4.66

#Rotatable Bonds: 11

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: 8.91

CX Basic pKa: ┄

CX LogP: 4.52

CX LogD: 4.51

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.12

Np Likeness Score: -0.80

References

1.  (2013)  Histone deacetylase inhibitors, 

Source

Source(1):

• BindingDB Database