epigallocatechin-(4β→8,2β→O-7)-epicatechin

CHEBI:65854 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A proanthocyanidin that is a doubly linked dimer composed of (−)-epicatechin and (−)-epigallocatechin as its flavanol units. Isolated from the wood of Xanthoceras sorbifolium, it exhibits inhibitory activity towards HIV-1 protease. — 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:26267 CHEBI:26267

Chemical structure

Computed structure properties
Molecular formula	C30H24O13
Charge	0
Average mass	592.509 Da
Monoisotopic mass	592.12169 Da
Source	ChEBI
InChIKey	WODBGULXKVZGQF-QCPBNORNSA-N

SMILES

[H][C@@]12c3c(O)cc(O)cc3O[C@@](c3cc(O)c(O)c(O)c3)(Oc3cc(O)c4c(c31)O[C@]([H])(c1ccc(O)c(O)c1)[C@H](O)C4)[C@@H]2O

InChI

InChI=1S/C30H24O13/c31-12-6-17(35)23-21(7-12)42-30(11-4-18(36)26(39)19(37)5-11)29(40)25(23)24-22(43-30)9-15(33)13-8-20(38)27(41-28(13)24)10-1-2-14(32)16(34)3-10/h1-7,9,20,25,27,29,31-40H,8H2/t20-,25-,27-,29-,30+/m1/s1

Also called

(2R,3R,8S,14R,15R)-2-(3,4-dihydroxyphenyl)-8-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8532288

Activity roles

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

CHEBI:35660 CHEBI:35660

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:65854`	epigallocatechin-(4β→8,2β→O-7)-epicatechin	`antibioticmech:chebi-b344a564eb`	2026-08-30

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:35660 (HIV protease 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.