pirazofurin

CHEBI:90284 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A C-glycosyl compound that is 4-hydroxy-1H-pyrazole-5-carboxamide in which the hydrogen at position 3 has been replaced by a β-D-ribofuranosyl group. — 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:20857
Label unavailable CHEBI:26410

Chemical structure

Computed structure properties
Molecular formula	C9H13N3O6
Charge	0
Average mass	259.218 Da
Monoisotopic mass	259.08044 Da
Source	ChEBI
InChIKey	XESARGFCSKSFID-FLLFQEBCSA-N

SMILES

NC(=O)c1nnc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1O

InChI

InChI=1S/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5-,7-,8+/m1/s1

Also called

pirazofurina (INN)— chebi
pirazofurine (INN)— chebi
pirazofurinum (INN)— chebi
(1S)-1,4-anhydro-1-(5-carbamoyl-4-hydroxy-1H-pyrazol-3-yl)-D-ribitol (EXACT_SYNONYM)— chebi
3-(β-D-ribofuranosyl)-4-hydroxypyrazole-5-carboxamide (EXACT_SYNONYM)— chebi
3-β-D-ribofuranosyl-4-hydroxypyrazole-5-carboxamide (EXACT_SYNONYM)— chebi
4-hydroxy-3-(β-D-ribofuranosyl)-1H-pyrazole-5-carboxamide (EXACT_SYNONYM)— chebi
4-hydroxy-3-β-D-ribofuranosyl-1H-pyrazole-5-carboxamide (EXACT_SYNONYM)— chebi
4-hydroxy-3-β-D-ribofuranosylpyrazole-5-carboxamide (EXACT_SYNONYM)— chebi
47599 (EXACT_SYNONYM)— chebi
Antibiotic A 23813 (EXACT_SYNONYM)— chebi
PF (EXACT_SYNONYM)— chebi
PZF (EXACT_SYNONYM)— chebi
compound 47599 (EXACT_SYNONYM)— chebi
pyrazofurin (EXACT_SYNONYM)— chebi
pyrazomycin (EXACT_SYNONYM)— chebi
β-pyrazomycin (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:30868-30-5
reaxys:827736

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

kegg.drug:D05658

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:90284`	pirazofurin	`antibioticmech:chebi-049b7252b6`	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
Streptomyces candidus NCBITaxon:67283	BGC0001985	Enzymatic assays compound specific	MIBIG 4.0.1 (entry 4)	questionable	MIBiG active entry; compound 'Pyrazofurin' joined by exact Standard InChIKey.	DOI:10.1002/anie.201910356 (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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (pirazofurin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces candidus)