semicochliodinol B

CHEBI:66462 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A bisindole alkaloid that is quinone bearing hydroxy substituents at positions 2 and 5 and two indol-3-yl groups at positions 3 and 6, one of which is carrying a prenyl group at position 6. Isolated from the culture broth of Chrysosporium merdarium, it acts as an inhibitor of HIV-1 protease and EGF-R protein tyrosine kinase. — 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:132126 CHEBI:132126
CHEBI:51879 CHEBI:51879

Chemical structure

Computed structure properties
Molecular formula	C27H22N2O4
Charge	0
Average mass	438.483 Da
Monoisotopic mass	438.15796 Da
Source	ChEBI
InChIKey	JWHQWQQROAZMII-UHFFFAOYSA-N

SMILES

CC(C)=CCc1ccc2c(C3=C(O)C(=O)C(c4cnc5ccccc45)=C(O)C3=O)cnc2c1

InChI

InChI=1S/C27H22N2O4/c1-14(2)7-8-15-9-10-17-19(13-29-21(17)11-15)23-26(32)24(30)22(25(31)27(23)33)18-12-28-20-6-4-3-5-16(18)20/h3-7,9-13,28-30,33H,8H2,1-2H3

Also called

2,5-dihydroxy-3-(1H-indol-3-yl)-6-[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione (EXACT_SYNONYM)— chebi

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:66462`	semicochliodinol B	`antibioticmech:chebi-25414035ea`	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.