nisin

CHEBI:71629 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A type-A lantibiotic containing 34 amino acid residues (including lanthionine (Lan), methyllanthionine (MeLan), didehydroalanine (Dha) and didehydroaminobutyric acid (Dhb)) and five thioether bridges. It is obtained by fermentation of the bacterium Lactococcus lactis and shows particular activity against Clostridium botulinum. It is used in the production of various processed foods to suppress Gram-positive spoilage and pathogenic bacteria and so extend shelf life. — 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:51026 CHEBI:51026
CHEBI:71645 CHEBI:71645

Chemical structure

Computed structure properties
Molecular formula	C143H230N42O37S7
Charge	0
Average mass	3354.139 Da
Monoisotopic mass	3351.5452 Da
Source	ChEBI
InChIKey	NVNLLIYOARQCIX-IPGQQNLLSA-N

SMILES

C=C(NC(=O)[C@@H](NC(=O)[C@H](Cc1cncn1)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@@H]1CS[C@@H](C)[C@H]2NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H]3CS[C@@H](C)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H]4CS[C@@H](C)[C@@H](NC(=O)[C@@H]5CSC[C@@H](NC(=O)/C(=C/C)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NC(=C)C(=O)N[C@@H](CC(C)C)C(=O)N5)C(=O)N5CCC[C@H]5C(=O)NCC(=O)N4)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N3)[C@H](C)SCC(NC2=O)C(=O)N[C@@H](Cc2cncn2)C(=O)N1)[C@@H](C)CC)C(C)C)C(=O)N[C@@H](CCCCN)C(=O)O

InChI

InChI=1S/C143H230N42O37S7/c1-24-69(11)105(148)135(213)162-82(27-4)118(196)174-94-58-225-59-95(175-123(201)89(48-67(7)8)169-115(193)74(16)158-138(216)107(70(12)25-2)180-132(94)210)133(211)184-112-79(21)229-61-96(160-104(190)56-152-134(212)100-38-34-44-185(100)142(112)220)128(206)164-84(36-29-32-42-145)120(198)182-109-76(18)226-60-97(161-103(189)55-151-117(195)85(39-45-223-22)165-122(200)88(47-66(5)6)168-113(191)72(14)156-102(188)54-153-136(109)214)129(207)171-92(51-101(147)187)125(203)166-86(40-46-224-23)119(197)163-83(35-28-31-41-144)121(199)183-110-77(19)228-63-99-130(208)170-90(49-80-52-149-64-154-80)124(202)176-98(62-227-78(20)111(141(219)177-99)181-116(194)75(17)159-140(110)218)131(209)173-93(57-186)127(205)179-108(71(13)26-3)139(217)172-91(50-81-53-150-65-155-81)126(204)178-106(68(9)10)137(215)157-73(15)114(192)167-87(143(221)222)37-30-33-43-146/h27,52-53,64-72,75-79,83-100,105-112,186H,15-16,24-26,28-51,54-63,144-146,148H2,1-14,17-23H3,(H2,147,187)(H,149,154)(H,150,155)(H,151,195)(H,152,212)(H,153,214)(H,156,188)(H,157,215)(H,158,216)(H,159,218)(H,160,190)(H,161,189)(H,162,213)(H,163,197)(H,164,206)(H,165,200)(H,166,203)(H,167,192)(H,168,191)(H,169,193)(H,170,208)(H,171,207)(H,172,217)(H,173,209)(H,174,196)(H,175,201)(H,176,202)(H,177,219)(H,178,204)(H,179,205)(H,180,210)(H,181,194)(H,182,198)(H,183,199)(H,184,211)(H,221,222)/b82-27-/t69-,70-,71-,72-,75-,76-,77-,78-,79-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94+,95-,96-,97-,98-,99?,100-,105-,106-,107-,108-,109+,110+,111+,112+/m0/s1

Also called

N-{[(1S,4S,7S,8S,11R,14S,17R,20S)-7-{[N2-({(3R,9S,12S,15S,21S,22S)-21-[(N2-{[(6R,9S,10S,15aS)-10-({[(3R,6S,12S,15S)-12-[(2S)-butan-2-yl]-6-isobutyl-15-{[(2Z)-2-(L-isoleucylamino)but-2-enoyl]amino}-9-methylene-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-lysyl)amino]-12-isobutyl-15,22-dimethyl-9-[2-(methylsulfanyl)ethyl]-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexaazacyclodocosan-3-yl}carbonyl)-L-asparaginyl-L-methionyl-L-lysyl]amino}-14-(1H-imidazol-5-ylmethyl)-4,8,20-trimethyl-3,6,12,15,21-pentaoxo-9,19-dithia-2,5,13,16,22-pentaazabicyclo[9.9.2]docos-17-yl]carbonyl}-L-seryl-L-isoleucyl-L-histidyl-N-(3-{[(1S)-5-amino-1-carboxypentyl]amino}-3-oxoprop-1-en-2-yl)-L-valinamide (EXACT_SYNONYM)— chebi
E234 (EXACT_SYNONYM)— chebi
EINECS 215-807-5 (EXACT_SYNONYM)— chebi
NSC 112903 (EXACT_SYNONYM)— chebi
NSC-112903 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:1414-45-5
patent:US2935503
reaxys:8188142
wikipedia.en:Nisin

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:33282 CHEBI:33282
CHEBI:65256 CHEBI:65256

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:71629`	nisin	`antibioticmech:chebi-10db9cb459`	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.