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.

CHEBI:59668 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

Equivalent identifiers for this same structure in other resources.

cas:59456-70-1
reaxys:4303204

Activity roles

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

CHEBI:25605 CHEBI:25605
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: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.