hyemaloside A

CHEBI:66051 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A β-D-glucoside compound having galloyl groups at positions 2, 3 and 6 and a 4-hydroxyphenyl substituent at the 1-position. Isolated from Eugenia hyemalis, it exhibits inhibitory activity against HIV-1. — 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.

CHEBI:22798 CHEBI:22798
CHEBI:37576 CHEBI:37576

Chemical structure

Computed structure properties
Molecular formula	C33H28O19
Charge	0
Average mass	728.568 Da
Monoisotopic mass	728.12248 Da
Source	ChEBI
InChIKey	DTLDDZWHEMEXCO-ILYYIXHASA-N

SMILES

O=C(OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H]1O)c1cc(O)c(O)c(O)c1

InChI

InChI=1S/C33H28O19/c34-15-1-3-16(4-2-15)49-33-29(52-32(47)14-9-21(39)26(43)22(40)10-14)28(51-31(46)13-7-19(37)25(42)20(38)8-13)27(44)23(50-33)11-48-30(45)12-5-17(35)24(41)18(36)6-12/h1-10,23,27-29,33-44H,11H2/t23-,27-,28+,29-,33-/m1/s1

Also called

4-hydroxyphenyl 2,3,6-tris-O-(3,4,5-trihydroxybenzoyl)-β-D-glucopyranoside (EXACT_SYNONYM)— chebi
2,3,6-tri-O-galloylarbutin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:19205163

Activity roles

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

CHEBI:52629 CHEBI:52629

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:66051`	hyemaloside A	`antibioticmech:chebi-2f3c3a6879`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:52629 (EC 3.1.26.13 (retroviral ribonuclease H) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — 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

Provenance

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