(S,E)-N-hydroxy-2-(5-(pent-1-enyl)-4-phenyl-1H-1,2,3-triazol-1-yl)-3-phenylpropanamide

ID: ALA4591041

PubChem CID: 155568542

Max Phase: Preclinical

Molecular Formula: C22H24N4O2

Molecular Weight: 376.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC/C=C/c1c(-c2ccccc2)nnn1[C@@H](Cc1ccccc1)C(=O)NO

Standard InChI:  InChI=1S/C22H24N4O2/c1-2-3-6-15-19-21(18-13-9-5-10-14-18)23-25-26(19)20(22(27)24-28)16-17-11-7-4-8-12-17/h4-15,20,28H,2-3,16H2,1H3,(H,24,27)/b15-6+/t20-/m0/s1

Standard InChI Key:  VDFITTYFVIOUKG-DIKFHFTNSA-N

Molfile:  

 
     RDKit          2D

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    4.9020   -9.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990   -9.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803   -9.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822   -8.7015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6249   -9.9149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188  -10.7680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641  -11.2666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371  -12.0431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6581  -12.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8942  -11.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6707  -10.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525  -12.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3314   -9.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774   -9.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0618   -9.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3594  -10.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765  -10.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019  -11.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7973  -10.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330  -13.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308  -14.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1465  -13.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4620  -13.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9622  -12.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2959  -11.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0705  -11.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6916  -11.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4662  -11.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  6 10  1  0
 10 11  1  0
  9 12  1  0
  2  6  1  0
  5 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 12  1  0
 11 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4591041

   ---

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: 376.46

Molecular Weight (Monoisotopic): 376.1899

AlogP: 4.05

#Rotatable Bonds: 8

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: 4.88

CX LogD: 4.86

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -0.50

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