(2S,3R,4R)-5-((S)-Acetylamino)-2,4-dihydroxy-6-((S)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

ID: ALA152452

PubChem CID: 656387

Max Phase: Phase

Molecular Formula: C11H19NO9

Molecular Weight: 309.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Aceneuramic acid | Sialic acid | NSC-111756 | UX-001 | UX001 | 5-Acetamido--3,5-dideoxy-D-glyceo-D-galacto-2-nonulosonic acid|NSC-111756|CHEMBL152452

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

Standard InChI:  InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6-,7+,8-,9+,11+/m0/s1

Standard InChI Key:  SQVRNKJHWKZAKO-USOVHJGOSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  1  0  0  0  0  0999 V2000
   -1.9750   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750   -0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -2.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2625   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    1.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250   -2.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    0.6083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208   -2.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583    0.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750   -3.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -4.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750   -1.1292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  1  1  0
  5  7  1  0
  6  1  1  0
  7  4  1  0
  8  2  1  0
  4  9  1  1
 10  9  1  0
 11  6  1  0
 12  8  2  0
 13 10  2  0
  2 14  1  6
  6 15  1  6
 16  8  1  0
  7 17  1  6
 11 18  1  1
 19 20  1  0
 20 11  1  0
 21 10  1  0
  1 22  1  1
  2  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA152452

   SIALIC 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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 309.27

Molecular Weight (Monoisotopic): 309.1060

AlogP: -3.87

#Rotatable Bonds: 5

Polar Surface Area: 176.78

Molecular Species: ACID

HBA: 8

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.00

CX Basic pKa: ┄

CX LogP: -3.56

CX LogD: -7.04

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.27

Np Likeness Score: 1.57

References

1. Masukawa KM, Kollman PA, Kuntz ID..  (2003)  Investigation of neuraminidase-substrate recognition using molecular dynamics and free energy calculations.,  46  (26): [PMID:14667217] [10.1021/jm030060q]

2. Johansson S, Nilsson E, Qian W, Guilligay D, Crepin T, Cusack S, Arnberg N, Elofsson M..  (2009)  Design, synthesis, and evaluation of N-acyl modified sialic acids as inhibitors of adenoviruses causing epidemic keratoconjunctivitis.,  52  (12): [PMID:19456100] [10.1021/jm801609s]

3. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates