rhizoxin

CHEBI:72590 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity. — 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.

macrolide antibiotic CHEBI:25105
Label unavailable CHEBI:32955
Label unavailable CHEBI:46812

Chemical structure

Computed structure properties
Molecular formula	C35H47NO9
Charge	0
Average mass	625.759 Da
Monoisotopic mass	625.32508 Da
Source	ChEBI
InChIKey	OWPCHSCAPHNHAV-QIPOKPRISA-N

SMILES

[H][C@]12CC(=O)O[C@]([H])(C1)[C@H](C)/C=C/[C@@]1([H])O[C@]1(C)[C@@H](O)C[C@@]([H])([C@H](C)[C@@H](OC)/C(C)=C/C=C/C(C)=C/c1coc(C)n1)OC(=O)[C@]1([H])O[C@@]1([H])C2

InChI

InChI=1S/C35H47NO9/c1-19(13-25-18-41-23(5)36-25)9-8-10-21(3)32(40-7)22(4)27-17-29(37)35(6)30(45-35)12-11-20(2)26-14-24(16-31(38)42-26)15-28-33(43-28)34(39)44-27/h8-13,18,20,22,24,26-30,32-33,37H,14-17H2,1-7H3/b9-8+,12-11+,19-13+,21-10+/t20-,22+,24+,26-,27+,28+,29+,30-,32+,33-,35-/m1/s1

Also called

(1S,3S,5R,8S,10S,11R,13R,14E,16R,17R)-10-hydroxy-8-[(2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-11,16-dimethyl-4,7,12,18-tetraoxatetracyclo[15.3.1.03,5.011,13]henicos-14-ene-6,19-dione (EXACT_SYNONYM)— chebi
Antibiotic WF-1360 (EXACT_SYNONYM)— chebi
WF-1360 (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.

cas:90996-54-6
reaxys:5915392

Activity roles

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

antimicrobial agent CHEBI:33281

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:72590`	rhizoxin	`antibioticmech:chebi-3434f13829`	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
Paraburkholderia rhizoxinica NCBITaxon:412963	BGC0001112	Enzymatic assays; Knock-out studies compound specific	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'rhizoxin A' joined by exact Standard InChIKey.	PMID:17154220 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

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

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (rhizoxin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Paraburkholderia rhizoxinica)