nikkomycin Z

CHEBI:623918 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A uridine-based nucleoside-peptide antibiotic which inhibits fungal chitin biosynthesis by inhibiting chitin synthase. — 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.

nikkomycin CHEBI:59668

Chemical structure

Computed structure properties
Molecular formula	C20H25N5O10
Charge	0
Average mass	495.445 Da
Monoisotopic mass	495.16014 Da
Source	ChEBI
InChIKey	WWJFFVUVFNBJTN-VHDFTHOZSA-N

SMILES

[H][C@]1([C@H](NC(=O)[C@@H](N)[C@H](C)[C@H](O)c2ccc(O)cn2)C(=O)O)O[C@@H](n2ccc(=O)nc2=O)[C@H](O)[C@@H]1O

InChI

InChI=1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12-,13-,14-,15+,16+,18+/m0/s1

Also called

(2S)-{[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino}-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-β-D-allo-furanuronic acid (EXACT_SYNONYM)— chebi
(2S)-{[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino}[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]acetic acid (EXACT_SYNONYM)— chebi
Neopolyoxin C (EXACT_SYNONYM)— chebi
Nikkomycin (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:59456-70-1
reaxys:4303204

Activity roles

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

nucleoside antibiotic CHEBI:25605
antifungal agent 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:623918`	nikkomycin Z	`antibioticmech:chebi-af0a3b64de`	2026-08-30

Mechanism summary

Mode of action: CELL_WALL_SYNTHESIS_INHIBITION microbial target — Assigned from ChEBI role CHEBI:59672 (EC 2.4.1.16 (chitin synthase) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — 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
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 (YAML).

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