N-(2-(cyclohexylamino)-2-oxoethyl)-N-(4-(hydroxycarbamoyl)benzyl)-1-naphthamide

ID: ALA4280840

PubChem CID: 145981954

Max Phase: Preclinical

Molecular Formula: C27H29N3O4

Molecular Weight: 459.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN(Cc1ccc(C(=O)NO)cc1)C(=O)c1cccc2ccccc12)NC1CCCCC1

Standard InChI:  InChI=1S/C27H29N3O4/c31-25(28-22-9-2-1-3-10-22)18-30(17-19-13-15-21(16-14-19)26(32)29-34)27(33)24-12-6-8-20-7-4-5-11-23(20)24/h4-8,11-16,22,34H,1-3,9-10,17-18H2,(H,28,31)(H,29,32)

Standard InChI Key:  MBFLWFXELLBKJM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.7853   -4.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4933   -4.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2030   -4.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2002   -3.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.6184   -4.4818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3268   -4.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0786   -3.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3710   -3.6653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6632   -3.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6630   -2.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9552   -2.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3706   -2.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6669   -5.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2472   -0.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9569   -1.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6653   -0.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6702    0.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9605    0.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2459    0.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2502   -4.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9565   -4.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9589   -3.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5487   -3.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5497   -4.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  4  7  1  0
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 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4280840

   ---

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: 459.55

Molecular Weight (Monoisotopic): 459.2158

AlogP: 4.05

#Rotatable Bonds: 7

Polar Surface Area: 98.74

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.52

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: -1.29

References

1. Diedrich D, Stenzel K, Hesping E, Antonova-Koch Y, Gebru T, Duffy S, Fisher G, Schöler A, Meister S, Kurz T, Avery VM, Winzeler EA, Held J, Andrews KT, Hansen FK..  (2018)  One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites.,  158  [PMID:30245402] [10.1016/j.ejmech.2018.09.018]

Source

Source(1):

• Scientific Literature