(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(1R,4S,7R,11R,14S,17R)-7-[(2S)-2-[(2S)-2-[(2S)-2-{[(3R,9S,12S,15S,21S)-21-[(2R)-2-{[(6R,10R,15aS)-10-[(3R,6S,12S,15R)-15-[(2E)-2-[(2S,3S)-2-amino-3-methylpentanamido]but-2-enamido]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraazacyclohexadecane-3-amido]-9-methyl-1,4,11-trioxo-tetradecahydropyrrolo[2,1-i]1-thia-4,7,10-triazacyclotridecan-6-yl]formamido}-6-aminohexanamido]-15,22-dimethyl-12-(2-methylpropyl)-9-[2-(methylsulfanyl)ethyl]-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexaazacyclodocosan-3-yl]formamido}-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-6-aminohexanamido]-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]docosan-17-yl]formamido}-3-hydroxypropanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanamido]-3-methylbutanamido]prop-2-enamido}-6-aminohexanoic acid

• ChemBase ID: 134206
• Molecular Formular: C143H230N42O37S7
• Molecular Mass: 3354.0705
• Monoisotopic Mass: 3351.54520351
• SMILES: CC[C@H](C)[C@H]1C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@@H](CSC[C@@H](C(=O)N1)NC(=O)/C(=C\C)/NC(=O)[C@H]([C@@H](C)CC)N)C(=O)N[C@H]1C(SC[C@H](NC(=O)CNC(=O)[C@@H]2CCCN2C1=O)C(=O)N[C@H](CCCCN)C(=O)N[C@@H]1C(SC[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC1=O)C)CC(C)C)CCSC)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@H]1C(SC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CSC([C@@H](C(=O)N2)NC(=O)[C@@H](NC1=O)C)C)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)Cc1cnc[nH]1)C)C)C)CC(C)C
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H]1C(C)SC[C@@H]2NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C)C(C)SC[C@H](NC(=O)[C@@H](NC2=O)Cc1cnc[nH]1)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NC(=C)C(=O)N[C@H](C(=O)O)CCCCN)C(C)C)Cc1cnc[nH]1)[C@H](CC)C)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CSC(C)[C@@H](NC(=O)[C@H](NC(=O)[C@@H]2CSC(C)[C@H](NC(=O)[C@@H]3CSC[C@H](NC(=O)/C(=C\C)/NC(=O)[C@H]([C@H](CC)C)N)C(=O)N[C@@H]([C@H](CC)C)C(=O)NC(=C)C(=O)N[C@H](C(=O)N3)CC(C)C)C(=O)N3[C@H](C(=O)NCC(=O)N2)CCC3)CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1)CCSC)CC(C)C)CC(=O)N)CCSC
• 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-ILAIHEEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(1R,4S,7R,11R,14S,17R)-7-[(2S)-2-[(2S)-2-[(2S)-2-{[(3R,9S,12S,15S,21S)-21-[(2R)-2-{[(6R,10R,15aS)-10-[(3R,6S,12S,15R)-15-[(2E)-2-[(2S,3S)-2-amino-3-methylpentanamido]but-2-enamido]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraazacyclohexadecane-3-amido]-9-methyl-1,4,11-trioxo-tetradecahydropyrrolo[2,1-i]1-thia-4,7,10-triazacyclotridecan-6-yl]formamido}-6-aminohexanamido]-15,22-dimethyl-12-(2-methylpropyl)-9-[2-(methylsulfanyl)ethyl]-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexaazacyclodocosan-3-yl]formamido}-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-6-aminohexanamido]-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]docosan-17-yl]formamido}-3-hydroxypropanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanamido]-3-methylbutanamido]prop-2-enamido}-6-aminohexanoic acid
• IUPAC Traditional name: (2S)-2-{2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(1R,4S,7R,11R,14S,17R)-7-[(2S)-2-[(2S)-2-[(2S)-2-{[(3R,9S,12S,15S,21S)-21-[(2R)-2-{[(6R,10R,15aS)-10-[(3R,6S,12S,15R)-15-[(2E)-2-[(2S,3S)-2-amino-3-methylpentanamido]but-2-enamido]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetraazacyclohexadecane-3-amido]-9-methyl-1,4,11-trioxo-decahydro-2H-pyrrolo[2,1-i]1-thia-4,7,10-triazacyclotridecan-6-yl]formamido}-6-aminohexanamido]-15,22-dimethyl-12-(2-methylpropyl)-9-[2-(methylsulfanyl)ethyl]-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexaazacyclodocosan-3-yl]formamido}-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-6-aminohexanamido]-14-(3H-imidazol-4-ylmethyl)-4,8,20-trimethyl-3,6,12,15,21-pentaoxo-9,19-dithia-2,5,13,16,22-pentaazabicyclo[9.9.2]docosan-17-yl]formamido}-3-hydroxypropanamido]-3-methylpentanamido]-3-(3H-imidazol-4-yl)propanamido]-3-methylbutanamido]prop-2-enamido}-6-aminohexanoic acid
• Synonyms: Nisin from Lactococcus lactis

Database IDs

• CAS Number: 1414-45-5
• MDL Number: MFCD00131724
• PubChem SID: 162228483; 24897751
• PubChem CID: 16219761

CALCULATED PROPERTIES

• Acid pKa: 3.404802
• H Acceptors: 43
• H Donor: 41
• LogD (pH = 5.5): -27.2917
• LogD (pH = 7.4): -23.547184
• Log P: -18.296362
• Molar Refractivity: 847.0992 cm^3
• Polarizability: 331.59427 Å^3
• Polar Surface Area: 1213.57 Å^2
• Rotatable Bonds: 67
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Concentration: 2.5% (balance sodium chloride and denatured milk solids)
• Potency: ≥1,000,000 per IU/g

DETAILS

Sigma Aldrich - N5764

Biochem/physiol Actions
Antibiotic with bactericidal action. Binds to the lipid A portion of bacterial lipopolysaccharides. Induces pore formation in the membranes of cortex cells from excised sorghum roots.Mode of Action: Binds to and interferes with the permeability of the cytoplasmic membrane.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria (requires chelator such as EDTA).
Nisin binds to cell wall precursor lipid components (lipid A portion) of bacteria and disrupts cell wall production. Nisin alters the cell membrane which results in the leakage of cytoplasmic components and destruction of the proton motive force1.
包装
Package size based on weight of total solids
Application
Nisin is a polycyclic lantibiotic produced by Lactococcus lactis. It is commonly used as a food preservative. It is used as a selective agent in cell culture for the isolation of gram-negative bacteria, yeast, and moulds. Product N54764 has been used in bioassays to study posttranslational modification of nisin1. Nisin is used to study food preservation.