cinnamycin

CHEBI:141991 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT REVIEWED

A type B lantibiotic consisting of a 19 amino acid tetracyclic polypeptide produced by Streptomyces cinnamoneus. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:24533
Label unavailable CHEBI:27532
Label unavailable CHEBI:51026
type B lantibiotic CHEBI:71647

Chemical structure

Computed structure properties
Molecular formula	C89H125N25O25S3
Charge	0
Average mass	2041.33 Da
Monoisotopic mass	2039.84406 Da
Source	ChEBI
InChIKey	QJDWKBINWOWJNZ-OURZNGJWSA-N

SMILES

[H][C@@]12NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H]([C@@H](O)C(=O)O)NC(=O)[C@@H]3CSC[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N)CS[C@H]1C)C(=O)N[C@H]1CS[C@@H](C)[C@@H](NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@@H]4CCCN4C(=O)CNC(=O)[C@H](Cc4ccccc4)NC(=O)[C@H](CNCCCC[C@@H](C(=O)O)NC2=O)NC1=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N3

InChI

InChI=1S/C89H125N25O25S3/c1-43(2)66-84(133)109-59-41-140-40-58-79(128)108-60-42-142-45(4)68(86(135)105-55(75(124)110-66)34-48-22-12-7-13-23-48)111-76(125)54(33-47-20-10-6-11-21-47)104-82(131)61-26-17-31-114(61)65(118)38-98-72(121)53(32-46-18-8-5-9-19-46)103-78(127)57(106-80(60)129)36-95-29-15-14-24-52(87(136)137)102-85(134)67(112-77(126)56(35-63(92)116)99-64(117)37-97-83(132)69(113-81(59)130)70(119)88(138)139)44(3)141-39-49(90)71(120)100-50(25-16-30-96-89(93)94)73(122)101-51(74(123)107-58)27-28-62(91)115/h5-13,18-23,43-45,49-61,66-70,95,119H,14-17,24-42,90H2,1-4H3,(H2,91,115)(H2,92,116)(H,97,132)(H,98,121)(H,99,117)(H,100,120)(H,101,122)(H,102,134)(H,103,127)(H,104,131)(H,105,135)(H,106,129)(H,107,123)(H,108,128)(H,109,133)(H,110,124)(H,111,125)(H,112,126)(H,113,130)(H,136,137)(H,138,139)(H4,93,94,96)/t44-,45-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58+,59-,60-,61-,66-,67+,68+,69-,70+/m0/s1

Also called

L-cysteinyl-L-arginyl-L-glutaminyl-D-cysteinyl-L-cysteinyl-3-aminoalanyl-L-phenylalanylglycyl-L-prolyl-L-phenylalanyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-phenylalanyl-L-valyl-L-cysteinyl-(3R)-3-hydroxy-L-a-aspartylglycyl-L-asparaginyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-lysine,cyclic (1→18),(4→14),(5→11)-tris(thioether),cyclic (6→19)-imine (EXACT_SYNONYM)— chebi
NSC 71936 (EXACT_SYNONYM)— chebi
NSC-71936 (EXACT_SYNONYM)— chebi
Ro 09-0198 (EXACT_SYNONYM)— chebi
Ro-09-0198 (EXACT_SYNONYM)— chebi
lanthiopeptin (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:110655-58-8
reaxys:18329075

Patents and articles

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

patent:US2004101963

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:141991`	cinnamycin	`antibioticmech:chebi-ac0986c8d7`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

phosphatidylethanolamine-containing membrane MEMBRANE DIRECT_BINDING_TARGET

Isothermal titration calorimetry measured a 1:1 complex and solid-state NMR showed loss of the normal bilayer organization in PE-containing membranes. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2002-02 (retrieved 2026-09-02).

PMID:11827543 (Primary cinnamycin-PE thermodynamic and solid-state-NMR study (DOI:10.1021/bi015841c).)

Mechanism summary

Mode of action: MEMBRANE_DISRUPTION host shared target — CURATOR: PMID:11827543 measured 1:1, high-affinity cinnamycin (Ro 09-0198) binding to phosphatidylethanolamine in model and biological membranes. Calorimetry and solid-state NMR showed that complex formation reorganizes the bilayer lipid matrix; phosphatidylethanolamine is shared by microbial and host membranes.

Record-level evidence

PMID:11827543 (Primary cinnamycin membrane-lipid binding and reorganization study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, antibiotic role, and unspecified filing class; added membrane disruption with direct phosphatidylethanolamine binding and explicit host-shared scope.
RESEEDED_FROM_SOURCES 2026-09-10 · 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).

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