(S)-2-(4-(4-tert-butylphenyl)-5-(cyclopropylethynyl)-1H-1,2,3-triazol-1-yl)-N-hydroxy-3-phenylpropanamide

ID: ALA4526387

PubChem CID: 155544048

Max Phase: Preclinical

Molecular Formula: C26H28N4O2

Molecular Weight: 428.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(-c2nnn([C@@H](Cc3ccccc3)C(=O)NO)c2C#CC2CC2)cc1

Standard InChI:  InChI=1S/C26H28N4O2/c1-26(2,3)21-14-12-20(13-15-21)24-22(16-11-18-9-10-18)30(29-27-24)23(25(31)28-32)17-19-7-5-4-6-8-19/h4-8,12-15,18,23,32H,9-10,17H2,1-3H3,(H,28,31)/t23-/m0/s1

Standard InChI Key:  LERROIJXRINUAL-QHCPKHFHSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    7.2185   -6.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5086   -6.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2231   -7.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699   -1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -2.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7501   -1.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -2.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868   -3.0996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4361   -3.5982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050   -4.3747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260   -4.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7621   -3.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5386   -3.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3110   -3.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0246   -5.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -1.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6494   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9297   -1.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -2.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444   -3.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -3.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -3.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0852   -2.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8928   -2.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6191   -2.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7009   -5.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1987   -6.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0145   -6.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3299   -5.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343   -4.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945   -7.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  1
  4  7  2  0
  4  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  9 13  1  0
 14 15  3  0
 13 14  1  0
 12 16  1  0
  5  9  1  0
  8 17  1  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 24  1  0
 25 24  1  0
 26 25  1  0
 24 26  1  0
 16 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 16  1  0
 29  2  1  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526387

   ---

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: 428.54

Molecular Weight (Monoisotopic): 428.2212

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 80.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.67

CX Basic pKa: ┄

CX LogP: 5.67

CX LogD: 5.64

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: -0.78

References

1. Ingham OJ, Paranal RM, Smith WB, Escobar RA, Yueh H, Snyder T, Porco JA, Bradner JE, Beeler AB..  (2016)  Development of a Potent and Selective HDAC8 Inhibitor.,  7  (10): [PMID:27774131] [10.1021/acsmedchemlett.6b00239]

Source

Source(1):

• Scientific Literature