N-acetyl-α-neuraminic acid

CHEBI:49026 ·resolve ·ANTIVIRAL ·EXACT SEEDED

N-Acetylneuraminic acid with α configuration at the anomeric centre. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

N-acetylneuraminic acid CHEBI:17012

Chemical structure

Computed structure properties
Molecular formula	C11H19NO9
Charge	0
Average mass	309.271 Da
Monoisotopic mass	309.10598 Da
Source	ChEBI
InChIKey	SQVRNKJHWKZAKO-YRMXFSIDSA-N

SMILES

[H][C@@]1([C@H](O)[C@H](O)CO)O[C@@](O)(C(=O)O)C[C@H](O)[C@H]1NC(C)=O

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

Also called

5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid (EXACT_SYNONYM)— chebi
5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosonic acid (EXACT_SYNONYM)— chebi
D-glycero-α-D-galacto-2-nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy- (EXACT_SYNONYM)— chebi
O-SIALIC ACID (EXACT_SYNONYM)— chebi
α-Neu5Ac (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

beilstein:1689968
glygen:G50850NI
glytoucan:G50850NI
pdb-ccd:SIA
reaxys:1689968

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

drugbank:DB03721

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

EC 3.2.1.18 (exo-α-sialidase) inhibitor CHEBI:52425

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:49026`	N-acetyl-α-neuraminic acid	`antibioticmech:chebi-07adfc19d4`	2026-08-30

Mechanism summary

Mode of action: VIRAL_RELEASE_INHIBITION host shared target — Assigned from ChEBI role CHEBI:52425 (EC 3.2.1.18 (exo-α-sialidase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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