4-((2-Acetyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)-N-hydroxybenzamide

ID: ALA4562244

PubChem CID: 50898671

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCc2c(c3ccccc3n2Cc2ccc(C(=O)NO)cc2)C1

Standard InChI:  InChI=1S/C21H21N3O3/c1-14(25)23-11-10-20-18(13-23)17-4-2-3-5-19(17)24(20)12-15-6-8-16(9-7-15)21(26)22-27/h2-9,27H,10-13H2,1H3,(H,22,26)

Standard InChI Key:  PLZLTKONMCWPLT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   40.8199  -29.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5279  -29.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2376  -29.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2347  -28.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5261  -28.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9459  -29.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9472  -30.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6530  -29.4598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.3613  -29.8673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1132  -28.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1130  -27.4173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5208  -26.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7719  -26.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5639  -27.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1103  -26.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8591  -25.7258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.0615  -25.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4513  -26.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7044  -26.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1618  -25.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3660  -25.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1157  -26.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6599  -27.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4068  -25.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2059  -25.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1555  -24.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 12 14  1  0
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 19 12  1  0
 13 14  2  0
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 15 16  1  0
 16 17  1  0
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 19 20  2  0
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 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 17 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4562244

   4-[(2-acetyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5-yl)methyl]-N-hydroxybenzamide

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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 2.71

#Rotatable Bonds: 3

Polar Surface Area: 74.57

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: 1.76

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -1.04

References

1. Géraldy M, Morgen M, Sehr P, Steimbach RR, Moi D, Ridinger J, Oehme I, Witt O, Malz M, Nogueira MS, Koch O, Gunkel N, Miller AK..  (2019)  Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated.,  62  (9): [PMID:30964290] [10.1021/acs.jmedchem.8b01936]

Source

Source(1):

• Scientific Literature