3-(1-phenethyl-1H-1,2,3-triazol-4-yl)1-carboxylic Acid Hydroxyamide

ID: ALA2178344

PubChem CID: 136030780

Max Phase: Preclinical

Molecular Formula: C17H16N4O2

Molecular Weight: 308.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)c1cccc(-c2cn(CCc3ccccc3)nn2)c1

Standard InChI:  InChI=1S/C17H16N4O2/c22-17(19-23)15-8-4-7-14(11-15)16-12-21(20-18-16)10-9-13-5-2-1-3-6-13/h1-8,11-12,23H,9-10H2,(H,19,22)

Standard InChI Key:  HWLOIPFPGVBJBC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   17.0548   -8.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7712   -8.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7684   -7.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0529   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3399   -8.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3411   -7.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4801   -8.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1952   -8.2306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4788   -9.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9091   -8.6442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6278   -8.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8743   -8.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3218   -8.9236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7337   -9.6385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5408   -9.4675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5013   -8.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1664   -8.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6519   -7.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4703   -7.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9556   -6.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6207   -6.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7958   -6.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3141   -6.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  2  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  5 11  1  0
 13 16  1  0
 16 17  1  0
 17 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
M  END

Alternative Forms

1. Parent:

   

   ALA2178344

   ---

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: 308.34

Molecular Weight (Monoisotopic): 308.1273

AlogP: 2.31

#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: 9.02

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.56

Np Likeness Score: -1.52

References

1. Suzuki T, Ota Y, Ri M, Bando M, Gotoh A, Itoh Y, Tsumoto H, Tatum PR, Mizukami T, Nakagawa H, Iida S, Ueda R, Shirahige K, Miyata N..  (2012)  Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries.,  55  (22): [PMID:23116147] [10.1021/jm300837y]

Source

Source(1):

• Scientific Literature