AntibioticMech

apiin

CHEBI:15932 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A β-D-glucoside having a β-D-apiosyl residue at the 2-position and a 5,4'-dihydroxyflavon-7-yl moiety at the anomeric position. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:22798 CHEBI:22798
• CHEBI:38686 CHEBI:38686
• CHEBI:50018 CHEBI:50018

Chemical structure

Computed structure properties

Molecular formula	C26H28O14
Charge	0
Average mass	564.496 Da
Monoisotopic mass	564.14791 Da
Source	ChEBI
InChIKey	NTDLXWMIWOECHG-YRCFQSNFSA-N

SMILES

O=c1cc(-c2ccc(O)cc2)oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3OC[C@](O)(CO)[C@H]3O)cc(O)c12

InChI

InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1

Also called

• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-β-D-glucopyranoside (EXACT_SYNONYM)— chebi
• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 3-C-(hydroxymethyl)-β-D-glycero-tetrofuranosyl-(1→2)-β-D-glucopyranoside (EXACT_SYNONYM)— chebi
• 5,7,4'-trihydroxyflavone 7-O-[β-D-apiosyl-(1→2)-β-D-glucoside] (EXACT_SYNONYM)— chebi
• 7-((2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone (EXACT_SYNONYM)— chebi
• 7-O-(beta-D-Apiofuranosyl-1,2-beta-D-glucosyl)-5,7,4'-trihydroxyflavone (EXACT_SYNONYM)— chebi
• 7-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one (EXACT_SYNONYM)— chebi
• Apiin (EXACT_SYNONYM)— chebi
• Apioside (EXACT_SYNONYM)— chebi
• apigenin 7-O-[β-D-apiosyl-(1→2)-β-D-glucoside] (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:26544-34-3
• hmdb:HMDB0030843
• kegg.compound:C04858
• knapsack:C00001019
• lincs.smallmolecule:LSM-18987
• lipidmaps:LMPK12110337
• metacyc.compound:7-O-BETA-D-APIOFURANOSYL-12-BETA-D-GLU
• patent:CN1284492
• patent:CN1413643
• reaxys:72966
• wikipedia.en:Apiin

Activity roles

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

• CHEBI:52425 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:15932	apiin	antibioticmech:chebi-0b3878ce15	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

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · 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.