(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-{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: 156104
• Molecular Formular: C143H230N42O37S7
• Molecular Mass: 3354.0705
• Monoisotopic Mass: 3351.54520351
• SMILES: CCC(C)C1C(=O)NC(=C)C(=O)NC(C(=O)NC(CSCC(C(=O)N1)NC(=O)C(=CC)NC(=O)C(C(C)CC)N)C(=O)NC1C(SCC(NC(=O)CNC(=O)C2CCCN2C1=O)C(=O)NC(CCCCN)C(=O)NC1C(SCC(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC1=O)C)CC(C)C)CCSC)C(=O)NC(CC(=O)N)C(=O)NC(CCSC)C(=O)NC(CCCCN)C(=O)NC1C(SCC2C(=O)NC(C(=O)NC(CSC(C(C(=O)N2)NC(=O)C(NC1=O)C)C)C(=O)NC(CO)C(=O)NC(C(C)CC)C(=O)NC(Cc1cnc[nH]1)C(=O)NC(C(C)C)C(=O)NC(=C)C(=O)NC(CCCCN)C(=O)O)Cc1cnc[nH]1)C)C)C)CC(C)C
• Canonical SMILES: NCCCCC(C(=O)NC1C(C)SCC2NC(=O)C(NC(=O)C(NC1=O)C)C(C)SCC(NC(=O)C(NC2=O)Cc1cnc[nH]1)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(=C)C(=O)NC(C(=O)O)CCCCN)C(C)C)Cc1cnc[nH]1)C(CC)C)CO)NC(=O)C(NC(=O)C(NC(=O)C1CSC(C)C(NC(=O)C(NC(=O)C2CSC(C)C(NC(=O)C3CSCC(NC(=O)C(=CC)NC(=O)C(C(CC)C)N)C(=O)NC(C(CC)C)C(=O)NC(=C)C(=O)NC(C(=O)N3)CC(C)C)C(=O)N3C(C(=O)NCC(=O)N2)CCC3)CCCCN)C(=O)NCC(=O)NC(C)C(=O)NC(C(=O)NC(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)
• InChIKey: NVNLLIYOARQCIX-UHFFFAOYSA-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-{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-{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: 162250242
• PubChem CID: 16133235

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
• Storage Temperature: 2-8°C

Product Information

• Compostion: denaturated milk solids, 22.5%; nisin, 2.5%; sodium chloride, 75%
• Empirical Formula (Hill Notation): C143H230N42O37S7

DETAILS

Sigma Aldrich - 72535

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).
Other Notes
Chemical and physical properties1; Applications, a literature survey2