3-[(Z)-2-isocyanovinyl]indole

CHEBI:140434 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A 3-(2-isocyanovinyl)indole in which the double bond of the isocyanovinyl group has Z (cis-) configuration. An antibacterial agent isolated from a species of Pseudomonas. — 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.

Label unavailable CHEBI:144370

Chemical structure

Computed structure properties
Molecular formula	C11H8N2
Charge	0
Average mass	168.199 Da
Monoisotopic mass	168.06875 Da
Source	ChEBI
InChIKey	JQMYMZZLIOIXEO-SREVYHEPSA-N

SMILES

[C-]#[N+]/C=C\c1cnc2ccccc12

InChI

InChI=1S/C11H8N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-8,13H/b7-6-

Also called

3-[(Z)-2-isocyanoethenyl]-1H-indole (EXACT_SYNONYM)— chebi
(Z) indolyl vinyl isonitrile (EXACT_SYNONYM)— chebi
(Z)-2-(1H-indol-3-yl)vinyl isocyanide (EXACT_SYNONYM)— chebi
B-371 (EXACT_SYNONYM)— chebi
antibiotic B-371 (EXACT_SYNONYM)— chebi
cis-indolyl vinyl isonitrile (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Activity roles

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

antibacterial agent CHEBI:33282

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:140434`	3-[(Z)-2-isocyanovinyl]indole	`antibioticmech:chebi-e84c38cdd2`	2026-08-30

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Hapalosiphon welwitschii NCBITaxon:1433842 strain UTEX B 1830	BGC0000668	Enzymatic assays; Heterologous expression cluster inherited	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound "3-(Z-2'-isocyanoethenyl)-indole" joined by exact Standard InChIKey.	DOI:10.1002/cbic.201300794 (MIBiG attaches this reference to the compound, as support for its STRUCTURE: every compound-level method in the release is structure elucidation (NMR, mass spectrometry, X-ray, total synthesis). It establishes what the molecule is. It is NOT evidence that this organism produces it; MIBiG attaches no reference to the producer link at all.)

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
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · 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 (YAML).

Explore across X-Mech: MediaIngredientMech (3-[(Z)-2-isocyanovinyl]indole) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Hapalosiphon welwitschii)