N-(4-(2-Butylhydrazine-1-carbonyl)benzyl)cinnamide

ID: ALA4757047

PubChem CID: 139575800

Max Phase: Preclinical

Molecular Formula: C21H25N3O2

Molecular Weight: 351.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCNNC(=O)c1ccc(CNC(=O)/C=C/c2ccccc2)cc1

Standard InChI:  InChI=1S/C21H25N3O2/c1-2-3-15-23-24-21(26)19-12-9-18(10-13-19)16-22-20(25)14-11-17-7-5-4-6-8-17/h4-14,23H,2-3,15-16H2,1H3,(H,22,25)(H,24,26)/b14-11+

Standard InChI Key:  NUJQZBBINFCTIV-SDNWHVSQSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   10.8380  -11.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1289  -12.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4198  -11.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7149  -12.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7149  -12.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0058  -13.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008  -12.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008  -12.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0058  -11.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8380  -10.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5471  -12.0670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2521  -11.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9612  -12.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6661  -11.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3752  -12.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3752  -12.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6661  -13.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9612  -12.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0843  -13.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0843  -14.1100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7934  -12.8842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4984  -13.2928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2074  -12.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9124  -13.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6276  -12.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3413  -13.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  1 10  2  0
  1 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 19 20  2  0
 21 22  1  0
 19 21  1  0
 23 24  1  0
 22 23  1  0
 16 19  1  0
 11 12  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757047

   ---

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: 351.45

Molecular Weight (Monoisotopic): 351.1947

AlogP: 3.05

#Rotatable Bonds: 9

Polar Surface Area: 70.23

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.90

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: -0.85

References

1. McClure JJ,Zhang C,Inks ES,Peterson YK,Li J,Chou CJ.  (2016)  Development of Allosteric Hydrazide-Containing Class I Histone Deacetylase Inhibitors for Use in Acute Myeloid Leukemia.,  59  (21): [PMID:27754681] [10.1021/acs.jmedchem.6b01385]

Source

Source(1):

• Scientific Literature