Compound ID | 2493

Update compound information

Cacaoidin

Class: Antimicrobial peptide

Spectrum of activity: Gram-positive
Details of activity: Active against methicillin-resistant Staphylococcus aureus, vancomycin-resistant enterococci, and Clostridium difficile; inhibits cell wall synthesis by binding to lipid II and murein transglycosylases
Description: Natural product from Streptomyces cacaoi ; lanthidin-type
Institute where first reported: Institute for Pharmaceutical Microbiology, University of Bonn, Meckenheimer Allee 168, 53115 Bonn, Germany
Year first mentioned: 2020
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 2374.74
Iso. SMILES: CC[C@@H](C)[C@@H](C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H]1[C@@H](S/C=C/NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC1=O)C)CO)CC2=CNC3=CC=CC=C32)C)NC(=O)[C@@H](C)NCC(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](C)NC(=O)[C@@H](CC4=CC=C(C=C4)O[C@@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)O)O[C@@H]6[C@H]([C@H]([C@@H]([C@@H](O6)C)O)O)O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC)NC(=O)[C@H]7CSC[C@H](C(=O)NC(=C)C(=O)N[C@@H](C(=O)N8CCCC8C(=O)N7)C)N(C)C
InChI Key: AIRSSZAIEIYYPQ-QBIWCITBSA-N
Can. SMILES: CC[C@@H](C)[C@@H](C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H]1[C@H](C)S/C=C/NC(=O)CNC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@@H](CO)NC(=O)[C@@H](C)NC1=O)NC(=O)[C@@H](C)NCC(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](C)NC(=O)[C@@H](CC4=CC=C(C=C4)O[C@@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)O)O[C@@H]6[C@H]([C@H]([C@@H]([C@H](C)O6)O)O)O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC)NC(=O)[C@H]7CSC[C@H](C(=O)NC(=C)C(=O)N[C@H](C)C(=O)N8CCCC8C(=O)N7)N(C)C
InChI: InChI=1S/C108H164N24O32S2/c1-23-48(6)78(103(157)119-55(13)90(144)115-58(16)94(148)130-80-62(20)166-38-36-109-76(135)43-112-95(149)70(40-64-41-111-68-30-27-26-29-66(64)68)123-98(152)71(44-133)125-92(146)56(14)120-105(80)159)128-87(141)51(9)110-42-75(134)50(8)113-88(142)54(12)118-102(156)77(47(4)5)127-93(147)57(15)114-89(143)52(10)116-97(151)69(39-63-32-34-65(35-33-63)163-108-85(140)86(82(137)61(19)162-108)164-107-84(139)83(138)81(136)60(18)161-107)124-104(158)79(49(7)24-2)129-96(150)67(25-3)122-99(153)72-45-165-46-74(131(21)22)101(155)117-53(11)91(145)121-59(17)106(160)132-37-28-31-73(132)100(154)126-72/h26-27,29-30,32-36,38,41,47-52,54-62,67,69-74,77-86,107-108,110-111,133,136-140H,11,23-25,28,31,37,39-40,42-46H2,1-10,12-22H3,(H,109,135)(H,112,149)(H,113,142)(H,114,143)(H,115,144)(H,116,151)(H,117,155)(H,118,156)(H,119,157)(H,120,159)(H,121,145)(H,122,153)(H,123,152)(H,124,158)(H,125,146)(H,126,154)(H,127,147)(H,128,141)(H,129,150)(H,130,148)/b38-36+/t48-,49+,50-,51-,52-,54+,55-,56-,57+,58+,59-,60+,61+,62+,67+,69-,70+,71-,72-,73?,74-,77+,78+,79+,80-,81-,82+,83+,84+,85-,86-,107-,108-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/156582301
Citations:
  • https://onlinelibrary.wiley.com/doi/10.1002/anie.202005187
  • https://www.cell.com/iscience/fulltext/S2589-0042(23)00471-6

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