myriocin

CHEBI:582124 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity. — 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:35785 CHEBI:35785
CHEBI:35868 CHEBI:35868
CHEBI:59755 CHEBI:59755
CHEBI:83925 CHEBI:83925

Chemical structure

Computed structure properties
Molecular formula	C21H39NO6
Charge	0
Average mass	401.544 Da
Monoisotopic mass	401.27774 Da
Source	ChEBI
InChIKey	ZZIKIHCNFWXKDY-GNTQXERDSA-N

SMILES

CCCCCCC(=O)CCCCCC/C=C/C[C@@H](O)[C@H](O)[C@@](N)(CO)C(=O)O

InChI

InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1

Also called

(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid (EXACT_SYNONYM)— chebi
(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoeicos-6-enoic acid (EXACT_SYNONYM)— chebi
(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid (EXACT_SYNONYM)— chebi
ISP-1 (EXACT_SYNONYM)— chebi
ISP-I (EXACT_SYNONYM)— chebi
antibiotic ISP-1 (EXACT_SYNONYM)— chebi
antibiotic ISP-I (EXACT_SYNONYM)— chebi
thermozymocidin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:35891-70-4
kegg.compound:C19914
knapsack:C00016936
lipidmaps:LMFA01060203
pdb-ccd:VRP
reaxys:5113331
wikipedia.en:Myriocin

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:582124`	myriocin	`antibioticmech:chebi-5019c40aa1`	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.