epidermin

CHEBI:71659 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A type A lantibiotic that is a tetracyclic 21-amino-acid peptide which contains meso-lanthionine, 3-methyllanthionine, and S-(2-aminovinyl)-D-cysteine. It is obtained from Staphylococcus epidermidis Tü 3298 and exhibits antibiotic activity against many Gram-positive bacteria. — 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:51026
type A lantibiotic CHEBI:71645

Chemical structure

Computed structure properties
Molecular formula	C98H141N25O23S4
Charge	0
Average mass	2165.626 Da
Monoisotopic mass	2163.9515 Da
Source	ChEBI
InChIKey	CXTXHTVXPMOOSW-JUEJINBGSA-N

SMILES

[H][C@@]12CCCN1C(=O)[C@H](NC(=O)[C@@H]1CSC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1)[C@H](C)SC[C@@]([H])(C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N/C(=C\C)C(=O)NCC(=O)N[C@@H]1CSC[C@@H]3NC(=O)[C@]([H])(Cc4ccc(O)cc4)NC(=O)[C@@H](CS/C=C\NC3=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc3ccccc3)NC1=O)NC(=O)CNC2=O

InChI

InChI=1S/C98H141N25O23S4/c1-9-51(4)77(102)96(144)107-54(7)81(129)117-70-48-149-49-71(120-97(145)78(52(5)10-2)121-89(137)65(40-57-25-16-13-17-26-57)113-85(133)62(112-92(70)140)28-19-21-35-100)94(142)122-79-55(8)150-50-72(109-76(127)44-105-95(143)73-29-22-37-123(73)98(79)146)90(138)106-53(6)80(128)111-61(27-18-20-34-99)84(132)110-60(11-3)82(130)104-43-75(126)108-68-47-148-46-67-83(131)103-36-38-147-45-69(93(141)115-64(87(135)118-67)41-58-30-32-59(124)33-31-58)119-88(136)66(42-74(101)125)116-86(134)63(114-91(68)139)39-56-23-14-12-15-24-56/h11-17,23-26,30-33,36,38,51-55,61-73,77-79,124H,9-10,18-22,27-29,34-35,37,39-50,99-100,102H2,1-8H3,(H2,101,125)(H,103,131)(H,104,130)(H,105,143)(H,106,138)(H,107,144)(H,108,126)(H,109,127)(H,110,132)(H,111,128)(H,112,140)(H,113,133)(H,114,139)(H,115,141)(H,116,134)(H,117,129)(H,118,135)(H,119,136)(H,120,145)(H,121,137)(H,122,142)/b38-36-,60-11-/t51-,52-,53-,54-,55-,61-,62-,63-,64-,65-,66-,67-,68+,69+,70+,71-,72-,73-,77-,78-,79+/m0/s1

Also called

N-({(6R,9S,10S,15aS)-10-[({(3R,6S,9S,12S,15S)-12-(4-aminobutyl)-9-benzyl-6-[(2S)-butan-2-yl]-15-[(L-isoleucyl-L-alanyl)amino]-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraazacyclohexadecan-3-yl}carbonyl)amino]-9-methyl-1,4,11-trioxododecahydro-1H,9H-pyrrolo[2,1-i][1,4,7,10]thiatriazacyclotridecin-6-yl}carbonyl)-L-alanyl-N-{(2Z)-1-[(2-{[(1S,4S,7S,10S,14R,17Z,23S)-4-(2-amino-2-oxoethyl)-7-benzyl-23-(4-hydroxybenzyl)-3,6,9,15,21,24-hexaoxo-12,19-dithia-2,5,8,16,22,25-hexaazabicyclo[12.6.5]pentacos-17-en-10-yl]amino}-2-oxoethyl)amino]-1-oxobut-2-en-2-yl}-L-lysinamide (EXACT_SYNONYM)— chebi
staphylococcin 1580 (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:99165-17-0
reaxys:11305595

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

patent:EP0350810

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial agent CHEBI:33282

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:71659`	epidermin	`antibioticmech:chebi-6352c2661c`	2026-08-30

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 1

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
EpiFEG-associated reduced susceptibility to epidermin The tested subjects are TM300-derived laboratory strains, not the unmodified background. Staphylococcus epidermidis Tue3298 is the donor. The three-component result does not establish individual sufficiency; transport remains a hypothesis. Donor references UniProtKB:Q54002 (EpiF), UniProtKB:Q54003 (EpiE) and UniProtKB:Q54004 (EpiG) are not experimental allele assignments. ENA lists the paper's U29130 as a secondary accession of U77778. No derivative TaxID, genome, numerical AST or clinical category is assigned.	—	Staphylococcus carnosus `NCBITaxon:1281`	epiF, epiE, epiG	PMID:8550476 (Author-uploaded primary text: Results, Table 1 and Discussion. Purified epidermin is named in the assay section. Figures and supplements were not visually inspected.) Source-reported growth susceptibility comparisons; qualitative result only

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 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-09 · codex · LLM-assisted
Added qualitative primary-backed resistance evidence with donor, host and substrate distinctions. Reference proteins are not assigned as exact experimental alleles. Existing chemical and source evidence preserved; whole-record review remains open.

Provenance

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

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