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Apamin

CAT: 0957-P1234-02Size: 25 mgDry Ice: YesHazardous: No
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Description
Apamin, an 18 amino acid peptide neurotoxin present in apitoxin (bee venom), has been shown to have anti-inflammatory and anti-fibrotic properties. It is known to be a highly selective blocker of Ca2+-activated K+ (SK) channels and then lessen the expression of α-SMA in the TGF-β1-induced HSC-T6 cells.
CAS Number
24345-16-2
Target
Potassium Channel
Activity
Transmembrane Transporters
Molecular Formula
C79H131N31O24S4
Storage Conditions
3 years -20°C powder; 1 years -80°C in solvent

Chemical Information

Apamin

Apamin is a component of bee venom and was originally isolated in the Western honey bee (Apis mellifera). It is a polypeptide neurotoxin that acts by blocking SK channels in the central nervous system. Apamin can have therapeutic applications, as the SK channels have been proposed as targets for the treatment of ataxia, epilepsy, memory disorders, and possibly schizophrenia and Parkinson's disease. (L1012)

CAS Number24345-16-2
PubChem CID16133797
IUPAC Name3-[(1R,4S,7S,13S,16S,19S,22S,25S,28R,31S,34S,37S,40R,47S,50R)-50-amino-40-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[[(2S)-1-amino-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamoyl]-4-(4-aminobutyl)-47-(2-amino-2-oxoethyl)-34,37-bis(3-carbamimidamidopropyl)-19-[(1R)-1-hydroxyethyl]-7,22,31-trimethyl-25-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,46,49-tetradecaoxo-42,43,52,53-tetrathia-3,6,9,15,18,21,24,27,30,33,36,39,45,48-tetradecazatricyclo[26.16.10.09,13]tetrapentacontan-16-yl]propanoic acid
Molecular FormulaC79H131N31O24S4
Molecular Weight2027.4
XLogP-13.4
Topological Polar Surface Area1020
Hydrogen Bond Donor Count31
Hydrogen Bond Acceptor Count33
Rotatable Bond Count37
Heavy Atom Count138
Formal Charge0
Complexity4320
SMILES
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)N[C@H](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](CC4=CNC=N4)C(=O)N)CCCNC(=N)N)CCCNC(=N)N
InChI
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
InChIKey
YVIIHEKJCKCXOB-STYWVVQQSA-N
Chemical Structure
2D Structure
2D structure of Apamin
CAS: 24345-16-2
CID: 16133797
Formula: C79H131N31O24S4
MW: 2027.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight2027.4
XLogP3-13.4
Hydrogen Bond Donor Count31
Hydrogen Bond Acceptor Count33
Rotatable Bond Count37
Exact Mass2025.8866089
Monoisotopic Mass2025.8866089
Topological Polar Surface Area1020 Ų
Heavy Atom Count138
Formal Charge0
Complexity4320
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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