rac-N-(4-(hydroxycarbamoyl)phenyl)-4-(naphthalen-2-yl)tetrahydro-2H-pyran-4-carboxamide

ID: ALA4642874

PubChem CID: 156016822

Max Phase: Preclinical

Molecular Formula: C23H22N2O4

Molecular Weight: 390.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(NC(=O)C2(c3ccc4ccccc4c3)CCOCC2)cc1

Standard InChI:  InChI=1S/C23H22N2O4/c26-21(25-28)17-6-9-20(10-7-17)24-22(27)23(11-13-29-14-12-23)19-8-5-16-3-1-2-4-18(16)15-19/h1-10,15,28H,11-14H2,(H,24,27)(H,25,26)

Standard InChI Key:  VNRCXPZNHIIBGH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.0515   -4.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0469   -5.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -5.7734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -5.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4817   -4.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3422   -4.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -3.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0565   -2.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404   -2.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4898   -3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2057   -4.1247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9203   -3.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6307   -4.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3448   -3.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3439   -2.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6231   -2.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9119   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0580   -2.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7744   -2.8785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4884   -2.4658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4885   -2.8859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0556   -1.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -3.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -2.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052   -2.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1929   -2.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -3.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219   -4.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 24  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 25  1  0
  8  1  1  0
  1 11  1  0
 11 12  1  0
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 13 14  2  0
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 16 17  1  0
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 18 13  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 11 22  2  0
 19 23  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4642874

   ---

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: 390.44

Molecular Weight (Monoisotopic): 390.1580

AlogP: 3.65

#Rotatable Bonds: 4

Polar Surface Area: 87.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.15

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -0.99

References

1. Tng J, Lim J, Wu KC, Lucke AJ, Xu W, Reid RC, Fairlie DP..  (2020)  Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class I HDAC Enzymes and Cancer Cell Proliferation.,  63  (11): [PMID:32383881] [10.1021/acs.jmedchem.0c00230]

Source

Source(1):

• Scientific Literature