メリチン【ミツバチ】

Melittin

HCID 16133648

基本情報

CAS: 20449-79-0
標準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
分子式: C131H229N39O31
平均分子量: 2,846.5 g/mol
単同位体質量: 2,844.75417155

概要

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.

名称と識別子

優先名称: 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
現地名: メリチン【ミツバチ】
英語名: MELITTIN
分子式: C131H229N39O31
分子量: 2846.47

名称と別名

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

名称をさらに表示

メリッチン【ミツバチ】メリッチンメリチン【ミツバチ】メリチン FROM HONEY BEE VENOMmelittenmelittiniC11198MELLITINmelittin(major)beevenommelittinhoneybeemelittin

Melittin (honeybee)ForapineForapinMelittin TFAMelittin IMFCD00076868Melittin (major)Melittin (apis cerana)

データベース識別子

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

物性

構造計算による物性

XLogP: -2.7
極性表面積: 1,150 Å²
水素結合供与体数: 41
水素結合受容体数: 37
回転可能結合数: 99
重原子数: 201
形式電荷: 0
複雑度: 6,300

実験および物理化学的性質

Collision Cross Section756.79 Å² [M+4H]4+ [CCS Type: DT; Method: stepped-field]

物理化学的性質

比旋光度: 21 · D21 -89.52° (c = 0.409)
比重(密度): 1.39 · 1.39
貯蔵温度: -20 °C · -20°C
溶解性: 1 mg/ml · Soluble to 1 mg/ml in 20% acetonitrile
外見: 白色からかすかな黄褐色の粉末。
色: White to off-white
由来生物: animal (Apis mellifera)
水溶解度: 1 mg/ml · Soluble to 1 mg/ml in water
化粧品成分の機能: 皮脂抑制
InChIKey: VDXZNPDIRNWWCW-JFTDCZMZSA-N

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory InformationMelittin: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Health Effects · 1 件

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 件

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)

安全データ

F: 10-21
wgk: 3
rtecs: OS3965000
ridadr: UN 3462 6.1/PG 1
risk_code: 23/24/25
hazard_code: T
safety_code: 36-45-36/37/39
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 Oral
ストレージクラス: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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.

用途と製造

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

応用分野

使用Melittin has been used in standard bacterium-killing assay to determine bactericidal activity and study the role of melittin in allergic reactions.

一般的な説明Chemical structure: peptide

上流・下流製品情報

上流原料

サプライヤー100 社

陕西文迪生物科技有限公司17391978915 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

陕西缔都新材料有限公司81124267 17392282731 · [email protected]

湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]

補足説明 · 1 件

定義ChEBI: 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 com onent of bee venom.

化合物ノート

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