N-acetylneuraminic acid

ID: ALA4280954

Chembl Id: CHEMBL4280954

Cas Number: 131-48-6

PubChem CID: 439197

Max Phase: Preclinical

Molecular Formula: C11H19NO9

Molecular Weight: 309.27

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(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-LUWBGTNYSA-N

Alternative Forms

1. Parent:

   

   ALA4280954

   N-Acetyl-Neuraminic 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: 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. Richards MR, Guo T, Hunter CD, Cairo CW..  (2018)  Molecular dynamics simulations of viral neuraminidase inhibitors with the human neuraminidase enzymes: Insights into isoenzyme selectivity.,  26  (19): [PMID:29903413] [10.1016/j.bmc.2018.05.035]

2. Dubois L, Pietrancosta N, Cabaye A, Fanget I, Debacker C, Gilormini PA, Dansette PM, Dairou J, Biot C, Froissart R, Goupil-Lamy A, Bertrand HO, Acher FC, McCort-Tranchepain I, Gasnier B, Anne C..  (2020)  Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.,  63  (15): [PMID:32608236] [10.1021/acs.jmedchem.9b02119]

3. Dubois L, Pietrancosta N, Cabaye A, Fanget I, Debacker C, Gilormini PA, Dansette PM, Dairou J, Biot C, Froissart R, Goupil-Lamy A, Bertrand HO, Acher FC, McCort-Tranchepain I, Gasnier B, Anne C..  (2020)  Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.,  63  (15): [PMID:32608236] [10.1021/acs.jmedchem.9b02119]

Source

Source(1):

• Scientific Literature