sinefungin

CHEBI:45453 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An adenosine that is the the δ-(5'-adenosyl) derivative of ornithine. — 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:22260 CHEBI:22260
CHEBI:83925 CHEBI:83925

Chemical structure

Computed structure properties
Molecular formula	C15H23N7O5
Charge	0
Average mass	381.393 Da
Monoisotopic mass	381.17607 Da
Source	ChEBI
InChIKey	LMXOHSDXUQEUSF-YECHIGJVSA-N

SMILES

Nc1ncnc2c1ncn2[C@@H]1O[C@H](C[C@@H](N)CC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O

InChI

InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1

Also called

sinefungina (INN)— chebi
sinefungine (INN)— chebi
sinefunginum (INN)— chebi
(5S)-5-amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-L-norleucine (EXACT_SYNONYM)— chebi
(2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid (EXACT_SYNONYM)— chebi
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid (EXACT_SYNONYM)— chebi
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid (EXACT_SYNONYM)— chebi
A 9145 (EXACT_SYNONYM)— chebi
ADENOSYL-ORNITHINE (EXACT_SYNONYM)— chebi
Antibiotic A 9145 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:58944-73-3
kegg.drug:D05846
metacyc.compound:SINEFUNGIN
patent:US3758681
patent:US5872104
pdb-ccd:SFG
reaxys:3574678

Activity roles

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

CHEBI:33281 CHEBI:33281
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:45453`	sinefungin	`antibioticmech:chebi-c266cf14d1`	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.