ambiguine I

CHEBI:65401 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An ambiguine that consists of a 5,5,7,10,10-pentamethyl-4,5,5a,6a,6b,7,8,9,9a,10-decahydro-10dH-6-oxa-4-azacyclopropa[6,7]cyclohepta[1,2,3,4-mno]aceanthrylen-10d-ol skeleton with an ethenyl substituent at position 7 and an isocyano group at position 6b (the 5aS,6aR,6bR,7R,9aR,10dR stereoisomer). An antimicrobial agent isolated from the cyanobacterium strain Fischerella. — 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:141618 CHEBI:141618
CHEBI:26878 CHEBI:26878
CHEBI:32955 CHEBI:32955
CHEBI:35353 CHEBI:35353
CHEBI:51914 CHEBI:51914

Chemical structure

Computed structure properties
Molecular formula	C26H30N2O2
Charge	0
Average mass	402.538 Da
Monoisotopic mass	402.23073 Da
Source	ChEBI
InChIKey	RVIIZRJMWFSNER-LJCLWVHTSA-N

SMILES

[H][C@]12O[C@@]1([H])C(C)(C)c1nc3cccc4c3c1[C@@]1(O)[C@@]2([N+]#[C-])[C@@](C)(C=C)CC[C@]1([H])C4(C)C

InChI

InChI=1S/C26H30N2O2/c1-8-24(6)13-12-16-22(2,3)14-10-9-11-15-17(14)18-19(28-15)23(4,5)20-21(30-20)26(24,27-7)25(16,18)29/h8-11,16,20-21,28-29H,1,12-13H2,2-6H3/t16-,20-,21+,24+,25-,26+/m1/s1

Also called

(5aS,6aR,6bR,7R,9aR,10dR)-7-ethenyl-6b-isocyano-5,5,7,10,10-pentamethyl-4,5,5a,6a,6b,7,8,9,9a,10-decahydro-10dH-6-oxa-4-azacyclopropa[6,7]cyclohepta[1,2,3,4-mno]aceanthrylen-10d-ol (EXACT_SYNONYM)— chebi
ambiguine I isonitrile (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

chemspider:17214461
reaxys:18851758

Activity roles

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

CHEBI:33282 CHEBI:33282
CHEBI:35718 CHEBI:35718

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:65401`	ambiguine I	`antibioticmech:chebi-5ad026b5ee`	2026-08-30

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.