Apamin

Apamin[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.041.969 Edit this at Wikidata
UNII
  • InChI=1S/C79H131N31O24S4/c1-35(2)26-49-70(127)107-51-31-136-135-30-41(81)63(120)105-50(28-57(84)114)71(128)108-53(73(130)99-42(12-7-8-22-80)64(121)96-38(5)77(134)110-25-11-15-54(110)75(132)102-47(18-21-58(115)116)69(126)109-59(39(6)111)76(133)95-37(4)62(119)104-49)33-138-137-32-52(106-66(123)44(14-10-24-92-79(88)89)98-65(122)43(13-9-23-91-78(86)87)97-61(118)36(3)94-72(51)129)74(131)101-45(16-19-55(82)112)67(124)100-46(17-20-56(83)113)68(125)103-48(60(85)117)27-40-29-90-34-93-40/h29,34-39,41-54,59,111H,7-28,30-33,80-81H2,1-6H3,(H2,82,112)(H2,83,113)(H2,84,114)(H2,85,117)(H,90,93)(H,94,129)(H,95,133)(H,96,121)(H,97,118)(H,98,122)(H,99,130)(H,100,124)(H,101,131)(H,102,132)(H,103,125)(H,104,119)(H,105,120)(H,106,123)(H,107,127)(H,108,128)(H,109,126)(H,115,116)(H4,86,87,91)(H4,88,89,92)/t36?,37-,38-,39+,41-,42-,43-,44?,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,59?/m0/s1 checkY
    Key: YVIIHEKJCKCXOB-WNKOHBQLSA-N checkY
  • InChI=1S/C79H131N31O24S4/c1-35(2)26-49-70(127)107-51-31-136-135-30-41(81)63(120)105-50(28-57(84)114)71(128)108-53(73(130)99-42(12-7-8-22-80)64(121)96-38(5)77(134)110-25-11-15-54(110)75(132)102-47(18-21-58(115)116)69(126)109-59(39(6)111)76(133)95-37(4)62(119)104-49)33-138-137-32-52(106-66(123)44(14-10-24-92-79(88)89)98-65(122)43(13-9-23-91-78(86)87)97-61(118)36(3)94-72(51)129)74(131)101-45(16-19-55(82)112)67(124)100-46(17-20-56(83)113)68(125)103-48(60(85)117)27-40-29-90-34-93-40/h29,34-39,41-54,59,111H,7-28,30-33,80-81H2,1-6H3,(H2,82,112)(H2,83,113)(H2,84,114)(H2,85,117)(H,90,93)(H,94,129)(H,95,133)(H,96,121)(H,97,118)(H,98,122)(H,99,130)(H,100,124)(H,101,131)(H,102,132)(H,103,125)(H,104,119)(H,105,120)(H,106,123)(H,107,127)(H,108,128)(H,109,126)(H,115,116)(H4,86,87,91)(H4,88,89,92)/t36?,37-,38-,39+,41-,42-,43-,44?,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,59?/m0/s1
  • Key: YVIIHEKJCKCXOB-WNKOHBQLSA-N
  • C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)NC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)N)C(=O)N1)CC(C)C)C)[C@@H](C)O)CCC(=O)O)C)CCCCN)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc4cnc[nH]4)C(=O)N)CCCNC(=N)N)CCCNC(=N)N
Properties
C79H131N31O24S4
Molar mass 2027.33874 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Apamin Preproprotein
Identifiers
SymbolApamin
CAS number24345-16-2
NCBI gene406135
UniProtP01500
Search for
StructuresSwiss-model
DomainsInterPro

Apamin is an 18 amino acid globular peptide neurotoxin found in apitoxin (bee venom).[2] Dry bee venom consists of 2–3% of apamin.[3] Apamin selectively blocks SK channels, a type of Ca2+-activated K+ channel expressed in the central nervous system. Toxicity is caused by only a few amino acids, in particular cysteine1, lysine4, arginine13, arginine14 and histidine18. These amino acids are involved in the binding of apamin to the Ca2+-activated K+ channel. Due to its specificity for SK channels, apamin is used as a drug in biomedical research to study the electrical properties of SK channels and their role in the afterhyperpolarizations occurring immediately following an action potential.[4]

  1. ^ Apamin - Compound Summary, PubChem.
  2. ^ Habermann E (1984). "Apamin". Pharmacology & Therapeutics. 25 (2): 255–70. doi:10.1016/0163-7258(84)90046-9. PMID 6095335.
  3. ^ Son DJ, Lee JW, Lee YH, Song HS, Lee CK, Hong JT (Aug 2007). "Therapeutic application of anti-arthritis, pain-releasing, and anti-cancer effects of bee venom and its constituent compounds". Pharmacology & Therapeutics. 115 (2): 246–70. doi:10.1016/j.pharmthera.2007.04.004. PMID 17555825.
  4. ^ Castle NA, Haylett DG, Jenkinson DH (Feb 1989). "Toxins in the characterization of potassium channels". Trends in Neurosciences. 12 (2): 59–65. doi:10.1016/0166-2236(89)90137-9. PMID 2469212. S2CID 22356085.