CHEBI:71629 - nisin

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ChEBI Name nisin
ChEBI ID CHEBI:71629
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C143H230N42O37S7
Net Charge 0
Average Mass 3354.07100
Monoisotopic Mass 3351.545
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
InChIKey NVNLLIYOARQCIX-IPGQQNLLSA-N
SMILES CC[C@H](C)[C@H](N)C(=O)N\C(=C/C)C(=O)N[C@@H]1CSC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)C(=C)NC(=O)[C@@H](NC1=O)[C@@H](C)CC)C(=O)N[C@@H]1[C@H](C)SC[C@H](NC(=O)CNC(=O)[C@@H]2CCCN2C1=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]1[C@H](C)SC[C@H](NC(=O)CNC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)CNC1=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]1[C@H](C)SCC2NC(=O)[C@H](NC(=O)[C@H](C)NC1=O)[C@H](C)SC[C@H](NC(=O)[C@H](Cc1cnc[nH]1)NC2=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](C(C)C)C(=O)NC(=C)C(=O)N[C@@H](CCCCN)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent
A substance that kills or slows the growth of bacteria.
antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
Application(s): antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nisin (CHEBI:71629) has role antibacterial agent (CHEBI:33282)
nisin (CHEBI:71629) has role antimicrobial food preservative (CHEBI:65256)
nisin (CHEBI:71629) has role metabolite (CHEBI:25212)
nisin (CHEBI:71629) is a macrocycle (CHEBI:51026)
nisin (CHEBI:71629) is a type A lantibiotic (CHEBI:71645)
IUPAC Name
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
Synonyms Sources
E234 ChEBI
EINECS 215-807-5 ChemIDplus
NSC 112903 ChemIDplus
NSC-112903 ChemIDplus
Database Links Databases
Nisin Wikipedia
US2935503 Patent
View more database links
Registry Numbers Types Sources
1414-45-5 CAS Registry Number ChemIDplus
8188142 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16247668 PubMed citation Europe PMC
21294231 PubMed citation Europe PMC
22265294 PubMed citation Europe PMC
22691226 PubMed citation Europe PMC
22850391 PubMed citation Europe PMC
Last Modified
01 February 2013