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melittin

Structure via PubChem · Public domain (PubChem)

EntityQ424512· pop 22· linked from 220 articles

melittin

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Also known as GIGAVLKVLTTGLPALISWIKRKRQQ-NH2, bee venom melittin, Honeybee melittin, Forapine, Forapin, melitten

Melittin is the main component (40–60% of the dry weight) and the major pain-producing substance of honeybee (Apis mellifera) venom. Melittin is a basic peptide consisting of 26 amino acids.

OverviewAI-generated

Melittin is a chemical compound with the formula C₁₃₁H₂₂₉N₃₉O₃₁. It is identified in scientific databases by the PubChem CID 16133648 and the InChIKey VDXZNPDIRNWWCW-JFTDCZMZSA-N.

The molecule has an XLogP value of -2.7 and a topological polar surface area (TPSA) of 1150. It contains 41 hydrogen bond donors and 37 hydrogen bond acceptors.

Synthesized by Vinony from 9 facts across 3 sources: Wikidata, PubMed, PubChem. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Protein family.Symbol
Melittin
Protein family.Name
Melittin
Protein family.image
PDB 2mlt EBI.jpg
Protein family.caption
Melittin
Protein family.Pfam
PF01372
Protein family.InterPro
IPR002116
Protein family.SCOP
2mlt
Protein family.TCDB
1.C.18
Protein family.OPM family
151
Protein family.OPM protein
2mlt

via Wikipedia infobox

Chemical data

Formula
C131H229N39O31
Molecular weight
2846.5 g/mol
IUPAC name
(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[2-[[(2S,3R)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]acetyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]acetyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]pentanediamide
SMILES
CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N)NC(=O)CN
InChIKey
VDXZNPDIRNWWCW-JFTDCZMZSA-N
XLogP
-2.7
Polar surface area
1150 Ų
H-bond donors
41
H-bond acceptors
37
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Protein

via ChEMBL · EBI

Protein · UniProt

Melittin

Gene
MELT
Organism
Apis mellifera (Honeybee)
Length
70 aa
Molecular mass
7,585 Da
Evidence
1: Evidence at protein level

Melittin: Main toxin of bee venom with strong antimicrobial activity and hemolytic activity (PubMed:24512991, PubMed:4057243, PubMed:5139482, PubMed:5794226). It has enhancing effects on bee venom phospholipase A2 activity (PubMed:4371280). This amphipathic toxin binds to negatively charged membrane surface and forms pore by inserting into lipid bilayers inducing the leakage of ions and molecules and the enhancement of permeability that ultimately leads to cell lysis (PubMed:3666135, PubMed:4057243, PubMed:6830776). It acts as a voltage-gated pore with higher selectivity for anions over cat…

3D-structureAllergenAmidationAntimicrobialCytolysisDirect protein sequencingFormylationHemolysis
View on UniProt →

Swiss-Prot (reviewed) · via UniProt

Research

3,399 papers

via PubMed

Wikidata facts

Part of
apitoxin
Mass
2845.757527
Show 6 more facts
chemical formula
C₁₃₁H₂₂₉N₃₉O₃₁
Commons category
Melittin
canonical SMILES
CCC(C)C(C(=O)NCC(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C(C)CC)C(=O)NC(CO)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)N)NC(=O)CN
found in taxon
Apis mellifera
active ingredient in
apitoxin
isomeric SMILES
CC[C@H](C)[C@H](NC(=O)CN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(N)=O)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)O)C(C)C)C(C)C
Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

8 sections
Contents
  • Function
  • Structure
  • Mechanism of action
  • Toxicity of a bee sting
  • Use
  • Gallery
  • References
  • External links

Melittin is the main component (40–60% of the dry weight) and the major pain-producing substance of honeybee (Apis mellifera) venom. Melittin is a basic peptide consisting of 26 amino acids.

== Function ==

Excerpted from Wikipedia’s “melittin” article, available under the CC BY-SA 4.0 licence.

Available in 21 languages

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via Wikidata sitelinks · CC0