(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编号: 134206
• 分子式: C143H230N42O37S7
• 平均质量: 3354.0705
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (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
• 别名: Nisin from Lactococcus lactis

登记号

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

理论计算性质

• Acid pKa: 3.404802
• 质子受体: 43
• 质子供体: 41
• LogD (pH = 5.5): -27.2917
• LogD (pH = 7.4): -23.547184
• Log P: -18.296362
• 摩尔折射率: 847.0992 cm^3
• 极化性: 331.59427 Å^3
• 极化表面积: 1213.57 Å^2
• 可自由旋转的化学键: 67
• 里宾斯基五规则: false

分子性质

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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.