Melittin

HCID 16133648CAS 20449-79-0
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Grundinformationen

Standard-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
InChIKey
VDXZNPDIRNWWCW-JFTDCZMZSA-N
Summenformel
C131H229N39O31
Durchschnittliche Molmasse
2.846,5 g/mol
Monoisotopische Masse
2.844,75417155

Überblick

Melittin is a 26-membered polypeptide consisting of Gly, Ile, Gly, Ala, Val, Leu, Lys, Val, Leu, Thr, Thr, Gly, Leu, Pro, Ala, Leu, Ile, Ser, Trp, Ile, Lys, Arg, Lys, Arg, Gln and Gln-NH2 residues joined in sequence. It is the principal active component of bee venom. It has a role as an antineoplastic agent, an EC 2.7.11.13 (protein kinase C) inhibitor, a hepatoprotective agent, a neuroprotective agent, an apoptosis inducer, an animal metabolite and a venom. It is a peptidyl amide and a polypeptide.

Namen und Bezeichner

Bevorzugter Name
Melittin
IUPAC
(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

Namen und Synonyme

MelittinHoneybee melittinBee venom melittinGIGAVLKVLTTGLPALISWIKRKRQQ-NH2CHEBI:673637231-28-0Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2DTXSID40893812RefChem:42360DTXCID101323858253-417-7(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
Weitere Namen anzeigen
Melittin (honeybee)ForapineForapinMelittin TFAMelittin IMFCD00076868Melittin (major)Melittin (apis cerana)

Datenbank-Bezeichner

CAS
20449-79-0、37231-28-0
PubChem CID
16133648
DTXSID
DTXSID001046261
ChEMBL
CHEMBL412927
ChEBI
CHEBI:6736
EC Number
253-417-7
Nikkaji
J390.575F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,7
Polarare Oberfläche (TPSA)
1.150 Ų
H-Brücken-Donoren
41
H-Brücken-Akzeptoren
37
Frei drehbare Bindungen
99
Schwere Atome
201

Experimentelle und physikochemische Eigenschaften

Collision Cross Section756.79 Ų [M+4H]4+ [CCS Type: DT; Method: stepped-field]

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationMelittin: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

Health Effects · 1 Eintrag

Melittin poisoning may cause development of optic neuritis and atrophy. Serious cases may lead to atrial fibrillation, cerebral infarction, acute myocardial infarction, Fisher's syndrome, Guillain-Barre syndrome, claw hand caused by Ulnar nerve entrapment, and haemorrhaging in the lungs. (L1012)

Exposure RoutesInjection (sting/bite) (L1811)
Toxicity Summary · 1 Eintrag

Melittin has strong haemolytic activity. It integrates into cell membranes and has multiple effects, probably, as a result of its interaction with negatively charged phospholipids. Melittin inhibits well known transport pumps such as the Na+-K+-ATPase and the H+-K+-ATPase, and increases the permeability of cell membranes to ions, particularly Na+ and indirectly Ca2+, because of the Na+-Ca2+-exchange. (A608)

Signs and SymptomsMelittin poisoning is characterized by burning or stinging pain, swelling, and redness at the site of the bee sting, and may be followed by swelling of the tongue and throat, difficulty breathing, and shock. (L1012)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 6.00 mg/kg (Intravenous, Mouse) (A686)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.

Verwendung und Herstellung

UsesMelittin is the main component of bee venom. (L1014)

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