Molecule ID: 70788963

IUPAC Name: (2S)-6-amino-2-[2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(1S,4S,7S,8S,14S,17R,20S)-7-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(3R,9S,12S,15S,21S,22S)-21-[[(2S)-6-amino-2-[[(3S,4S,7R,13S)-3-[[(3R,6S,12S,15S)-15-[[(Z)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]but-2-enoyl]amino]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetrazacyclohexadecane-3-carbonyl]amino]-4-methyl-2,9,12-trioxo-5-thia-1,8,11-triazabicyclo[11.3.0]hexadecane-7-carbonyl]amino]hexanoyl]amino]-15,22-dimethyl-12-(2-methylpropyl)-9-(2-methylsulfanylethyl)-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexazacyclodocosane-3-carbonyl]amino]-4-oxobutanoyl]amino]-4-methylsulfanylbutanoyl]amino]hexanoyl]amino]-14-(1H-imidazol-5-ylmethyl)-4,8,20-trimethyl-3,6,12,15,21-pentaoxo-9,19-dithia-2,5,13,16,22-pentazabicyclo[9.9.2]docosane-17-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylbutanoyl]amino]prop-2-enoylamino]hexanoic acid

Description: The molecule is 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. It has a role as an antimicrobial food preservative, a metabolite and an antibacterial agent. It is a macrocycle and a type A lantibiotic.

SMILES: C=C(N=C(O)[C@@H](N=C(O)[C@H](Cc1cnc[nH]1)N=C(O)[C@@H](N=C(O)[C@H](CO)N=C(O)[C@@H]1CS[C@@H](C)[C@H]2N=C(O)[C@H](C)N=C(O)[C@H](N=C(O)[C@H](CCCCN)N=C(O)[C@H](CCSC)N=C(O)[C@H](CC(=N)O)N=C(O)[C@@H]3CS[C@@H](C)[C@@H](N=C(O)[C@H](CCCCN)N=C(O)[C@@H]4CS[C@@H](C)[C@@H](N=C(O)[C@@H]5CSC[C@@H](N=C(O)/C(=C/C)N=C(O)[C@@H](N)[C@@H](C)CC)C(O)=N[C@@H]([C@@H](C)CC)C(O)=NC(=C)C(O)=N[C@@H](CC(C)C)C(O)=N5)C(=O)N5CCC[C@H]5C(O)=NCC(O)=N4)C(O)=NCC(O)=N[C@@H](C)C(O)=N[C@@H](CC(C)C)C(O)=N[C@@H](CCSC)C(O)=NCC(O)=N3)[C@H](C)SCC(N=C2O)C(O)=N[C@@H](Cc2cnc[nH]2)C(O)=N1)[C@@H](C)CC)C(C)C)C(O)=N[C@@H](CCCCN)C(=O)O

SELFIES: [C][=C][Branch3][Ring1][=Branch2][#Branch1][N][=C][Branch1][C][O][C@@H1][Branch3][Ring1][Branch2][Branch2][N][=C][Branch1][C][O][C@H1][Branch1][=Branch2][C][C][=C][N][=C][NH1][Ring1][Branch1][N][=C][Branch1][C][O][C@@H1][Branch3][Ring1][=Branch1][Branch2][N][=C][Branch1][C][O][C@H1][Branch1][Ring1][C][O][N][=C][Branch1][C][O][C@@H1][C][S][C@@H1][Branch1][C][C][C@H1][N][=C][Branch1][C][O][C@H1][Branch1][C][C][N][=C][Branch1][C][O][C@H1][Branch2][P][Branch2][N][=C][Branch1][C][O][C@H1][Branch1][=Branch1][C][C][C][C][N][N][=C][Branch1][C][O][C@H1][Branch1][Branch1][C][C][S][C][N][=C][Branch1][C][O][C@H1][Branch1][#Branch1][C][C][=Branch1][C][=N][O][N][=C][Branch1][C][O][C@@H1][C][S][C@@H1][Branch1][C][C][C@@H1][Branch2][#Branch2][#Branch2][N][=C][Branch1][C][O][C@H1][Branch1][=Branch1][C][C][C][C][N][N][=C][Branch1][C][O][C@@H1][C][S][C@@H1][Branch1][C][C][C@@H1][Branch2][#Branch1][Ring2][N][=C][Branch1][C][O][C@@H1][C][S][C][C@@H1][Branch2][Ring1][#Branch2][N][=C][Branch1][C][O][/C][=Branch1][Ring1][=C][/C][N][=C][Branch1][C][O][C@@H1][Branch1][C][N][C@@H1][Branch1][C][C][C][C][C][Branch1][C][O][=N][C@@H1][Branch1][#Branch1][C@@H1][Branch1][C][C][C][C][C][Branch1][C][O][=N][C][=Branch1][C][=C][C][Branch1][C][O][=N][C@@H1][Branch1][#Branch1][C][C][Branch1][C][C][C][C][Branch1][C][O][=N][Ring2][Ring2][N][C][=Branch1][C][=O][N][C][C][C][C@H1][Ring1][Branch1][C][Branch1][C][O][=N][C][C][Branch1][C][O][=N][Ring2][=Branch1][Ring1][C][Branch1][C][O][=N][C][C][Branch1][C][O][=N][C@@H1][Branch1][C][C][C][Branch1][C][O][=N][C@@H1][Branch1][#Branch1][C][C][Branch1][C][C][C][C][Branch1][C][O][=N][C@@H1][Branch1][Branch1][C][C][S][C][C][Branch1][C][O][=N][C][C][Branch1][C][O][=N][Ring2][=Branch2][Branch1][C@H1][Branch1][C][C][S][C][C][Branch1][#Branch1][N][=C][Ring2][N][C][O][C][Branch1][C][O][=N][C@@H1][Branch1][=Branch2][C][C][=C][N][=C][NH1][Ring1][Branch1][C][Branch1][C][O][=N][Ring2][=N][Branch1][C@@H1][Branch1][C][C][C][C][C][Branch1][C][C][C][C][Branch1][C][O][=N][C@@H1][Branch1][=Branch1][C][C][C][C][N][C][=Branch1][C][=O][O]

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

Molecular Properties:
- Polar Surface Area: 1390.0 Ų
- LogP: -6.1