Compound: beta-neuraminic acid
SMILES: O=C(O)[C@]1(O[C@H]([C@H](N)[C@H](C1)O)[C@H](O)[C@H](O)CO)O
InChIKey: CERZMXAJYMMUDR-YOQZMRDMSA-N
Synonyms: beta-neuraminic acid, 497-43-8, 66774M69YT, CHEBI:49022, DTXSID401316250, RefChem:119471, GlyTouCan:G70854DZ, DTXCID301746113, G70854DZ, UNII-66774M69YT, 5-amino-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid, neuraminsaure, O-sialate, I(2)-Neuraminic acid, SCHEMBL24835, .BETA.-NEURAMINIC ACID, Methyl beta-neuraminic acid,methyl ester, HY-113017, CS-0059362, Q2823295, 5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonate, 5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acid, D-Glycero-.beta.-D-galacto-2-nonulopyranosonic acid, 5-amino-3,5-dideoxy-, (2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid
Theoretical properties:
molecular_formula: C9H17NO8
molecular_weight: 267.23 g/mol
exact_mass: 267.09541650 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 4
heavy_atom_count: 18
topological_polar_surface_area: 174 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 180.0 - 182.0 °C
Descriptions:
{"pubchem": "Beta-neuraminic acid is a 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid.", "chebi": null, "chembl": null, "wikipedia": "Neuraminic acid (5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulosonic acid) is an acidic (in particular ulosonic) amino sugar with a backbone formed by nine carbon atoms. Although nine-carbon sugars do not occur naturally, neuraminic acid may be regarded as a theoretical nine-carbon ketose in which the first link of the chain (the \u2013CH2OH at position 1) is oxidised into a carboxyl group (\u2013C(=O)OH), the hydroxyl group at position 3 is deoxidised (oxygen is removed from it), and the hydroxyl group at position 5 is substituted with an amino group (\u2013NH2). Neuraminic acid may also be visualized as the product of an aldol-condensation of pyruvic acid and D-mannosamine (2-amino-2-deoxy-mannose). \nNeuraminic acid does not occur naturally, but many of its derivatives are found widely distributed in animal tissues and in bacteria, especially in glycoproteins and gangliosides. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant form in mammalian cells being N-acetylneuraminic acid. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found.\nThe name \"neuraminic acid\" was introduced by German scientist E. Klenk in 1941, in reference to the brain lipids from which it was derived as a cleavage product.\nThe IUPAC symbol used for neuraminic acid is Neu, and the residue is typically found with additional chemical modifications in biological systems. As a family, these residues are known as sialic acids. For example, N-acetylneuraminic acid, Neu5Ac, is typical in human glycoproteins.\nAmong their many biological functions, these structures are substrates for neuraminidase enzymes which cleave neuraminic acid residues. Human flu viruses have a neuraminidase enzyme, signified in the name \"H#N#\", where the H refers to an isoform of hemagglutinin and N refers to an isoform of viral neuraminidase."}