5-Hexanamido-9-acetamido-2,6-anhydro-3,5-dideoxy-Dglycero-D-galactonon-2-enonic Acid

ID: ALA4290253

PubChem CID: 145989099

Max Phase: Preclinical

Molecular Formula: C17H28N2O8

Molecular Weight: 388.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CNC(C)=O)OC(C(=O)O)=C[C@@H]1O

Standard InChI:  InChI=1S/C17H28N2O8/c1-3-4-5-6-13(23)19-14-10(21)7-12(17(25)26)27-16(14)15(24)11(22)8-18-9(2)20/h7,10-11,14-16,21-22,24H,3-6,8H2,1-2H3,(H,18,20)(H,19,23)(H,25,26)/t10-,11+,14+,15+,16+/m0/s1

Standard InChI Key:  NLZZGCLVJKTGEH-IQVWLFHZSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   18.6518  -16.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3464  -16.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3189  -15.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6036  -14.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9089  -15.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9295  -16.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0136  -14.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7336  -15.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9882  -14.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1900  -14.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8863  -14.5352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1670  -14.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4941  -15.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4481  -13.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8630  -13.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4252  -12.9368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2348  -16.5949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2601  -17.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5655  -17.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9802  -17.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6795  -17.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8454  -17.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1507  -17.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4307  -17.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7063  -12.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0103  -12.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6833  -11.7314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7360  -17.9299    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  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
  5 11  1  1
 10 12  1  0
 10 13  1  6
 12 14  1  0
 12 15  1  1
 14 16  1  0
  6 17  1  1
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  6
 19 22  1  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
 25 27  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4290253

   ---

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: 388.42

Molecular Weight (Monoisotopic): 388.1846

AlogP: -1.36

#Rotatable Bonds: 10

Polar Surface Area: 165.42

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.20

CX Basic pKa: ┄

CX LogP: -1.94

CX LogD: -5.39

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.25

Np Likeness Score: 0.86

References

1. Guo T, Héon-Roberts R, Zou C, Zheng R, Pshezhetsky AV, Cairo CW..  (2018)  Selective Inhibitors of Human Neuraminidase 1 (NEU1).,  61  (24): [PMID:30457869] [10.1021/acs.jmedchem.8b01411]

2.  (2018)  Methods of preventing or treating atherosclerosis with inhibitors of specific isoenzymes of human neuraminidase, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data