tunicamycin A1

CHEBI:64245 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A nucleoside that is one of the homologues in the mixture that is tunicamycin, characterised by a 12-methyltridec-2-enoyl fatty acyl substituent on the amino group of the tunicamine moiety. — 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:33838 CHEBI:33838

Chemical structure

Computed structure properties
Molecular formula	C37H60N4O16
Charge	0
Average mass	816.899 Da
Monoisotopic mass	816.40043 Da
Source	ChEBI
InChIKey	YJQCOFNZVFGCAF-LLXUUZRASA-N

SMILES

[H][C@]1([C@]([H])(O)C[C@H]2O[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3NC(C)=O)[C@H](NC(=O)/C=C/CCCCCCCCC(C)C)[C@@H](O)[C@H]2O)O[C@@H](n2ccc(=O)nc2=O)[C@H](O)[C@@H]1O

InChI

InChI=1S/C37H60N4O16/c1-18(2)12-10-8-6-4-5-7-9-11-13-23(45)39-26-30(50)27(47)21(54-36(26)57-35-25(38-19(3)43)29(49)28(48)22(17-42)55-35)16-20(44)33-31(51)32(52)34(56-33)41-15-14-24(46)40-37(41)53/h11,13-15,18,20-22,25-36,42,44,47-52H,4-10,12,16-17H2,1-3H3,(H,38,43)(H,39,45)(H,40,46,53)/b13-11+/t20-,21-,22-,25-,26-,27+,28-,29-,30-,31+,32-,33-,34-,35-,36+/m1/s1

Also called

(2E)-N-[(2S,3R,4R,5R,6R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-{(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-2-hydroxyethyl}-4,5-dihydroxytetrahydro-2H-pyran-3-yl]-12-methyltridec-2-enamide (EXACT_SYNONYM)— chebi
(5'R)-5'-[2-acetamido-2-deoxy-α-D-glucopyranosyl-(1↔1)-2,6-dideoxy-2-(12-methyltridec-2-enamido)-β-D-galactopyranos-6-yl]uridine (EXACT_SYNONYM)— chebi
tunicamycin C (EXACT_SYNONYM)— chebi
tunicamycin II (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8183793

Activity roles

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

CHEBI:33281 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:64245`	tunicamycin A1	`antibioticmech:chebi-b2afcf7508`	2026-08-30

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.