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A9459

Apamin

Name: Apamin
Brand: SIGMA

synthetic, ≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):

C₇₉H₁₃₁N₃₁O₂₄S₄

CAS Number:

24345-16-2

Molecular Weight:

2027.34

NACRES:

NA.32

PubChem Substance ID:

24891455

UNSPSC Code:

12352200

MDL number:

MFCD00167944

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Properties

biological source

synthetic

Quality Segment

200

assay

≥97% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]2CCC[N@H]2C(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]3CSSC[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CSSC[C@H](N)C(=O)N[C@@H](CC(N)=O)C(=O)N3)NC1=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc4cnc[nH]4)C(N)=O)[C@@H](C)O

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

InChI key

YVIIHEKJCKCXOB-STYWVVQQSA-N

Gene Information

rat ... Kcnn1(54261)

Description

General description

Apamin, a bee venom is a polypeptide, that is made of 18 amino acids with two disulfide bridges.

Application

Apamin has been used in microbiological assays for the determination of antimicrobial activity of synthetic apamin and as a standard for MALDI (matrix-assisted laser desorption/ionization matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF MS) and electrospray ionisation mass spectrometry (ESI-MS) analysis.

Biochem/physiol Actions

The only polypeptide neurotoxin that is known to pass the blood-brain barrier. Blocks ATP-type Ca⁺²-activated K⁺ channels.

Apamin is a neurotoxin which can pass the blood-brain barrier. In human, it might cause peripheral nerve dysfunction, mainly seen after bee stings.

Other Notes

Lyophilized from 0.1% TFA in H2O

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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