2-deoxy-2,3-dehydro-i-acetylneuraminic acid

ID: ALA116550

PubChem CID: 5329058

Max Phase: Preclinical

Molecular Formula: C11H17NO8

Molecular Weight: 291.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@@H](O)[C@@H](O)CO)OC(C(=O)O)=C[C@@H]1O

Standard InChI:  InChI=1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6-,8+,9-,10+/m0/s1

Standard InChI Key:  JINJZWSZQKHCIP-LAVLCPKXSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.7451    1.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7451    0.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0307    0.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117    0.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117    1.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0307    2.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    3.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320   -0.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596    0.5821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4606    2.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625    3.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8894    2.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6028    1.8171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740    0.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4596   -0.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -0.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7451   -0.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497    2.6489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1176    1.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  2 10  1  1
  4  5  2  0
  1 11  1  0
  5  6  1  0
 11 12  1  6
 11 13  1  0
  1  2  1  0
 13 14  1  0
 13 16  1  1
  1  6  1  0
 14 15  1  0
  7 21  1  0
  7  8  2  0
 10 17  1  0
  5  7  1  0
 17 18  1  0
  2  3  1  0
 17 19  2  0
  3  9  1  6
  1 20  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA116550

   (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1S,2S)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

Molecule Features

Natural Product: Yes

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: 291.26

Molecular Weight (Monoisotopic): 291.0954

AlogP: -3.07

#Rotatable Bonds: 5

Polar Surface Area: 156.55

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.28

CX Basic pKa: ┄

CX LogP: -3.69

CX LogD: -7.12

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.31

Np Likeness Score: 1.44

References

1. Magesh S, Moriya S, Suzuki T, Miyagi T, Ishida H, Kiso M.  (2010)  Use of structure-based virtual screening in the investigation of novel human sialidase inhibitors,  19  (9): [10.1007/s00044-009-9269-6]

Source

Source(1):

• Scientific Literature