integrastatin A

CHEBI:66079 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An organic heterotetracyclic compound that is 6H-6,12-epoxydibenzo[b,f]oxocin-11(12H)-one substituted by hydroxy groups at positions 4, 7 and 8, a hydroxymethyl group position 1, methyl groups at positions 6 and 12 and methoxy groups at positions 3 and 9. It is isolated as a racemate from Unidentified fungi (New mexico) and has been shown to exhibit inhibitory activity against HIV-1 integrase. — 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:15734 CHEBI:15734
CHEBI:26195 CHEBI:26195
CHEBI:35618 CHEBI:35618
CHEBI:35990 CHEBI:35990
CHEBI:37407 CHEBI:37407
CHEBI:38163 CHEBI:38163
CHEBI:3992 CHEBI:3992

Chemical structure

Computed structure properties
Molecular formula	C20H20O9
Charge	0
Average mass	404.371 Da
Monoisotopic mass	404.11073 Da
Source	ChEBI
InChIKey	LNYIJBSSELCSKA-UHFFFAOYSA-N

SMILES

COc1cc2c(c(O)c1O)C1(C)Oc3c(O)c(OC)cc(CO)c3C(C)(O1)C2=O

InChI

InChI=1S/C20H20O9/c1-19-12-8(7-21)5-10(26-3)15(23)17(12)28-20(2,29-19)13-9(18(19)25)6-11(27-4)14(22)16(13)24/h5-6,21-24H,7H2,1-4H3

Also called

4,7,8-trihydroxy-1-(hydroxymethyl)-3,9-dimethoxy-6,12-dimethyl-6H-6,12-epoxydibenzo[b,f]oxocin-11(12H)-one (EXACT_SYNONYM)— chebi
rac-4,7,8-trihydroxy-1-(hydroxymethyl)-3,9-dimethoxy-6,12-dimethyl-6H-6,12-epoxydibenzo[b,f]oxocin-11(12H)-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:9166117

Activity roles

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

CHEBI:67268 CHEBI:67268

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:66079`	integrastatin A	`antibioticmech:chebi-768e7ef972`	2026-08-30

Mechanism summary

Mode of action: VIRAL_INTEGRASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:67268 (HIV-1 integrase 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.