N-hydroxy-4-((6-morpholino-1,3-dioxo-1H-benzo[d,e]isoquinolin-2(3H)-yl)methyl)benzamide

ID: ALA4176291

PubChem CID: 145973368

Max Phase: Preclinical

Molecular Formula: C24H21N3O5

Molecular Weight: 431.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(CN2C(=O)c3cccc4c(N5CCOCC5)ccc(c34)C2=O)cc1

Standard InChI:  InChI=1S/C24H21N3O5/c28-22(25-31)16-6-4-15(5-7-16)14-27-23(29)18-3-1-2-17-20(26-10-12-32-13-11-26)9-8-19(21(17)18)24(27)30/h1-9,31H,10-14H2,(H,25,28)

Standard InChI Key:  AHBZRNHYXZOOBT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    3.6930   -4.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4039   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4039   -3.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148   -2.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8257   -3.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8257   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148   -4.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930   -5.3868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821   -4.1555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5365   -2.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474   -3.3347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9583   -2.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6690   -3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6690   -4.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802   -4.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802   -5.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6694   -5.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9586   -5.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9586   -4.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0911   -4.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0911   -3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3806   -2.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9583   -2.1032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5363   -4.5661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2239   -5.3859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5130   -5.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8021   -5.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8021   -4.5651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5130   -4.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2239   -4.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821   -3.3347    0.0000 O   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
  2  7  2  0
  1  8  2  0
  1  9  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11 20  1  0
 15 20  2  0
 21 22  2  0
 22 23  1  0
 14 23  2  0
 16 21  1  0
 13 24  2  0
 11 25  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 26 31  1  0
 21 29  1  0
 10 12  1  0
  5 10  1  0
  9 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4176291

   ---

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: 431.45

Molecular Weight (Monoisotopic): 431.1481

AlogP: 2.59

#Rotatable Bonds: 4

Polar Surface Area: 99.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -1.15

References

1. Zhang Y, Yan J, Yao TP..  (2017)  Discovery of a fluorescent probe with HDAC6 selective inhibition.,  141  [PMID:29102179] [10.1016/j.ejmech.2017.10.022]

Source

Source(1):

• Scientific Literature