N-glycolylneuraminic acid

ID: ALA496421

Cas Number: 1113-83-3

PubChem CID: 123802

Product Number: G115995, Order Now?

Max Phase: Preclinical

Molecular Formula: C11H19NO10

Molecular Weight: 325.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: N-Glycolylneuraminic Acid | GcNeu|1113-83-3|NeuGc|NGNA|N-glycolyl-beta-neuraminic acid|CHEBI:62084|N-Glycolyl Neuraminic Acid|N-glycoloyl-beta-neuraminic acid|MFCD00057551|(2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid|(2S,4S,5R,6R)-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid|885329-49-7|(2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydrShow More⌵

Canonical SMILES:  O=C(CO)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/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1

Standard InChI Key:  FDJKUWYYUZCUJX-AJKRCSPLSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.5271    0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599    0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9554    1.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2336    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5164    1.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5118    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9416    1.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949    2.6512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8028    1.4011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6772   -0.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2556   -1.0530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735   -1.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6845   -1.0412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171   -0.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8071    0.5835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258   -1.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896    0.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6980   -2.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2 12  1  1
  5  6  1  0
 12 13  1  0
 13 14  1  0
  5  7  1  0
 13 15  2  0
  1  2  1  0
  1 16  1  0
  5  8  1  1
  1 17  1  1
  1  6  1  0
 16 18  1  0
  2  3  1  0
 16 19  1  6
  7  9  1  0
 18 20  1  1
  7 10  2  0
 18 21  1  0
  3  4  1  0
 21 22  1  0
  3 11  1  6
 14 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA496421

   N-Glycolylneuraminic 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: 325.27

Molecular Weight (Monoisotopic): 325.1009

AlogP: -4.90

#Rotatable Bonds: 6

Polar Surface Area: 197.01

Molecular Species: ACID

HBA: 9

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.92

CX Basic pKa: ┄

CX LogP: -4.38

CX LogD: -7.86

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.23

Np Likeness Score: 1.54

References

1. 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]

Source

Source(1):

• Scientific Literature