tunicamycin B1

CHEBI:64248 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A nucleoside that is one of the homologues in the mixture that is tunicamycin, characterised by a pentadec-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.

Label unavailable CHEBI:33838

Chemical structure

Computed structure properties
Molecular formula	C38H62N4O16
Charge	0
Average mass	830.926 Da
Monoisotopic mass	830.41608 Da
Source	ChEBI
InChIKey	QYVMTFXNKNWWFX-YGTZKZKGSA-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/CCCCCCCCCCCC)[C@@H](O)[C@H]2O)O[C@@H](n2ccc(=O)nc2=O)[C@H](O)[C@@H]1O

InChI

InChI=1S/C38H62N4O16/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-24(46)40-27-31(51)28(48)22(55-37(27)58-36-26(39-20(2)44)30(50)29(49)23(19-43)56-36)18-21(45)34-32(52)33(53)35(57-34)42-17-16-25(47)41-38(42)54/h14-17,21-23,26-37,43,45,48-53H,3-13,18-19H2,1-2H3,(H,39,44)(H,40,46)(H,41,47,54)/b15-14+/t21-,22-,23-,26-,27-,28+,29-,30-,31-,32+,33-,34-,35-,36-,37+/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]pentadec-2-enamide (EXACT_SYNONYM)— chebi
(5'R)-5'-[2-acetamido-2-deoxy-α-D-glucopyranosyl-(1↔1)-2,6-dideoxy-2-(pentadec-2-enamido)-β-D-galactopyranos-6-yl]uridine (EXACT_SYNONYM)— chebi
tunicamycin IV (EXACT_SYNONYM)— chebi

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:64248`	tunicamycin B1	`antibioticmech:chebi-e067ccc802`	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 chartreusis NCBITaxon:1079985 strain NRRL 3882	BGC0000880	Enzymatic assays; Heterologous expression; Knock-out studies compound specific	MIBIG 4.0.1 (entry 4)	questionable	MIBiG active entry; compound 'tunicamycin B1' joined by exact Standard InChIKey.	PMID:22717438 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

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

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (tunicamycin B1) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces chartreusis)