Compound ID | 3362

Update compound information

Tachyplesin I

Class: Antimicrobial peptide (cationic beta-hairpin)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Staphylococcus aureus and Escherichia coli; membrane-active agent and may inhibit FabG
Description: Natural product from horseshoe crab Tachypleus tridentatus; shows cytotoxicity towards human erythrocytes at very high concentrations (10x MIC; similar to gramicidin S)
Year first mentioned: 1993
Development status: Experimental
Chemical structure(s):
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Molecular weight: 2263.75
Iso. SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1)CCCNC(=N)N)CC3=CC=C(C=C3)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)CC4=CC=C(C=C4)O)CCCNC(=N)N)CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CCCCN)N)CC7=CC=CC=C7)CCCNC(=N)N)C(C)C
InChI Key: ZJQFYZCNRTZAIM-PMXBASNASA-N
Can. SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@@H](CC3=CC=C(C=C3)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N1)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H](CSSC[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC5=CC=C(C=C5)O)NC2=O)NC(=O)[C@H](CC6=CNC7=C6C=CC=C7)NC(=O)[C@H](CCCCN)N
InChI: InChI=1S/C99H151N35O19S4/c1-5-53(4)78-94(153)132-75-51-157-156-50-74(91(150)127-69(43-55-28-32-58(135)33-29-55)85(144)121-64(24-14-38-114-96(105)106)81(140)119-47-76(137)133-78)131-93(152)77(52(2)3)134-84(143)67(27-17-41-117-99(111)112)124-86(145)68(42-54-18-7-6-8-19-54)126-90(149)73(130-88(147)71(125-80(139)61(101)21-11-12-36-100)45-57-46-118-62-22-10-9-20-60(57)62)49-155-154-48-72(89(148)120-63(79(102)138)23-13-37-113-95(103)104)129-83(142)66(26-16-40-116-98(109)110)122-82(141)65(25-15-39-115-97(107)108)123-87(146)70(128-92(75)151)44-56-30-34-59(136)35-31-56/h6-10,18-20,22,28-35,46,52-53,61,63-75,77-78,118,135-136H,5,11-17,21,23-27,36-45,47-51,100-101H2,1-4H3,(H2,102,138)(H,119,140)(H,120,148)(H,121,144)(H,122,141)(H,123,146)(H,124,145)(H,125,139)(H,126,149)(H,127,150)(H,128,151)(H,129,142)(H,130,147)(H,131,152)(H,132,153)(H,133,137)(H,134,143)(H4,103,104,113)(H4,105,106,114)(H4,107,108,115)(H4,109,110,116)(H4,111,112,117)/t53-,61-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,77-,78-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16129721
Citations:
  • https://pmc.ncbi.nlm.nih.gov/articles/PMC5938390/
  • https://www.jstage.jst.go.jp/article/bpb1993/16/2/16_2_178/_article/-char/en

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