ethyl 2-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate

CHEBI:141398 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A member of the class of pyrazolopyrimidines that is pyrazophos in which the the thiophosphate group has been hydrolysed to the corresponding hydroxy group. The active fungicide of the profungicide pyrazophos. — 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:23990 CHEBI:23990
CHEBI:33822 CHEBI:33822
CHEBI:38669 CHEBI:38669

Chemical structure

Computed structure properties
Molecular formula	C10H11N3O3
Charge	0
Average mass	221.216 Da
Monoisotopic mass	221.08004 Da
Source	ChEBI
InChIKey	ZUAAVNLKGAEZDG-UHFFFAOYSA-N

SMILES

CCOC(=O)c1cn2nc(O)cc2nc1C

InChI

InChI=1S/C10H11N3O3/c1-3-16-10(15)7-5-13-8(11-6(7)2)4-9(14)12-13/h4-5H,3H2,1-2H3,(H,12,14)

Also called

5-methyl-2-oxo-1,2-dihydro-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester (EXACT_SYNONYM)— chebi
ethyl 5-methyl-2-oxo-1,2-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:57615-05-1
reaxys:887640

Activity roles

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

CHEBI:24127 CHEBI:24127
CHEBI:86328 CHEBI:86328

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:141398`	ethyl 2-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate	`antibioticmech:chebi-d25d49bacf`	2026-08-30

Mechanism summary

Mode of action: CELL_MEMBRANE_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:83741 (phospholipid biosynthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — 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.