(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(1S,7S,8S,11R,14R,17R,20S)-7-[(2S)-2-[(2S)-2-[(2S)-2-{[(3R,9S,12S,15S,21S,22S)-21-[(2S)-2-{[(6R,9S,10S,15aS)-10-[(3R,6S,12S,15S)-15-[(2E)-2-[(2S,3S)-2-amino-3-methylpentanamido]but-2-enamido]-6,12-bis[(2S)-butan-2-yl]-9-methylidene-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}-5-hydrazinylpentanamido]-12-[(2S)-butan-2-yl]-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]formamido}-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-6-aminohexanamido]-14-(1H-imidazol-5-ylmethyl)-8,20-dimethyl-4-methylidene-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: 128609
• Molecular Formular: C142H227N43O37S7
• Molecular Mass: 3353.04268
• Monoisotopic Mass: 3350.52480242
• SMILES: NCCCC[C@H](NC(=O)C(=C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H]1NC(=O)[C@@H](Cc2cnc[nH]2)NC(=O)[C@@H]2CS[C@H]([C@H](C(=O)NC(=C)C(=O)N[C@@H](C(=O)N2)[C@@H](SC1)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)NC(=O)[C@H]1CS[C@H]([C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1)CCSC)[C@H](CC)C)C)NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)CNC(=O)[C@@H]2CCCN2C(=O)[C@H](NC(=O)[C@@H]2NC(=O)[C@@H](NC(=O)C(=C)NC(=O)[C@@H](NC(=O)[C@@H](CSC2)NC(=O)/C(=C\C)/NC(=O)[C@H]([C@@H](C)CC)N)[C@@H](C)CC)[C@@H](C)CC)[C@@H](SC1)C)CCCNN)C)CCSC)CCCCN)C)[C@@H](C)CC)Cc1[nH]cnc1)C(=O)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@@H]1[C@H](C)SC[C@@H]2NC(=O)[C@H](NC(=O)C(=C)NC1=O)[C@H](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]1CS[C@@H](C)[C@H](NC(=O)[C@@H](NC(=O)[C@@H]2CS[C@@H](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)[C@H](CC)C)C(=O)N3[C@H](C(=O)NCC(=O)N2)CCC3)CCCNN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1)CCSC)[C@H](CC)C)CC(=O)N)CCSC
• InChI: InChI=1S/C142H227N43O37S7/c1-24-66(9)102(146)132(211)162-81(29-6)117(196)172-91-57-225-58-92(174-138(217)106(69(12)27-4)178-114(193)73(16)158-135(214)104(67(10)25-2)180-129(91)208)130(209)184-111-78(21)229-60-93(160-101(190)55-151-131(210)97-39-35-45-185(97)141(111)220)125(204)164-83(38-34-44-155-147)120(199)182-108-75(18)226-59-94(161-100(189)54-150-116(195)84(40-46-223-22)166-136(215)105(68(11)26-3)177-113(192)71(14)156-99(188)53-152-133(108)212)126(205)169-89(50-98(145)187)122(201)165-85(41-47-224-23)118(197)163-82(36-30-32-42-143)119(198)183-109-76(19)228-62-96-127(206)168-87(48-79-51-148-63-153-79)121(200)173-95(61-227-77(20)110(140(219)175-96)181-115(194)74(17)159-139(109)218)128(207)171-90(56-186)124(203)179-107(70(13)28-5)137(216)170-88(49-80-52-149-64-154-80)123(202)176-103(65(7)8)134(213)157-72(15)112(191)167-86(142(221)222)37-31-33-43-144/h29,51-52,63-71,75-78,82-97,102-111,155,186H,15-17,24-28,30-50,53-62,143-144,146-147H2,1-14,18-23H3,(H2,145,187)(H,148,153)(H,149,154)(H,150,195)(H,151,210)(H,152,212)(H,156,188)(H,157,213)(H,158,214)(H,159,218)(H,160,190)(H,161,189)(H,162,211)(H,163,197)(H,164,204)(H,165,201)(H,166,215)(H,167,191)(H,168,206)(H,169,205)(H,170,216)(H,171,207)(H,172,196)(H,173,200)(H,174,217)(H,175,219)(H,176,202)(H,177,192)(H,178,193)(H,179,203)(H,180,208)(H,181,194)(H,182,199)(H,183,198)(H,184,209)(H,221,222)/b81-29+/t66-,67-,68-,69-,70-,71-,75-,76-,77-,78-,82-,83-,84-,85-,86-,87+,88-,89-,90-,91+,92-,93-,94-,95-,96?,97-,102-,103-,104-,105-,106-,107-,108+,109+,110+,111+/m0/s1
• InChIKey: HZQRATOABKBXJZ-WHLDIHAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(1S,7S,8S,11R,14R,17R,20S)-7-[(2S)-2-[(2S)-2-[(2S)-2-{[(3R,9S,12S,15S,21S,22S)-21-[(2S)-2-{[(6R,9S,10S,15aS)-10-[(3R,6S,12S,15S)-15-[(2E)-2-[(2S,3S)-2-amino-3-methylpentanamido]but-2-enamido]-6,12-bis[(2S)-butan-2-yl]-9-methylidene-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}-5-hydrazinylpentanamido]-12-[(2S)-butan-2-yl]-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]formamido}-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-6-aminohexanamido]-14-(1H-imidazol-5-ylmethyl)-8,20-dimethyl-4-methylidene-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-{[(1S,7S,8S,11R,14R,17R,20S)-7-[(2S)-2-[(2S)-2-[(2S)-2-{[(3R,9S,12S,15S,21S,22S)-21-[(2S)-2-{[(6R,9S,10S,15aS)-10-[(3R,6S,12S,15S)-15-[(2E)-2-[(2S,3S)-2-amino-3-methylpentanamido]but-2-enamido]-6,12-bis[(2S)-butan-2-yl]-9-methylidene-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}-5-hydrazinylpentanamido]-12-[(2S)-butan-2-yl]-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]formamido}-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-6-aminohexanamido]-14-(3H-imidazol-4-ylmethyl)-8,20-dimethyl-4-methylidene-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

Database IDs

• CAS Number: 1414-45-5
• PubChem SID: 162222916
• PubChem CID: 44567786; 16219761
• CHEMBL: 526744
• Chemspider ID: 21106355
• Unique Ingredient Identifier: EN8XKG133D
• Wikipedia Title: Nisin

CALCULATED PROPERTIES

• Acid pKa: 3.4021246
• H Acceptors: 44
• H Donor: 42
• LogD (pH = 5.5): -25.146393
• LogD (pH = 7.4): -21.559309
• Log P: -18.499557
• Molar Refractivity: 857.7401 cm^3
• Polarizability: 330.85785 Å^3
• Polar Surface Area: 1225.6 Å^2
• Rotatable Bonds: 67
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: powder
• Boiling Point: 2966°C
• Density: 1.402 g/mL