(2S,3R,4R,6E)-2-アミノ-3,4-ジヒドロキシ-2-(ヒドロキシメチル)-14-オキソ-6-イコセン酸
Myriocin
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基本情報
- CAS
35891-70-4- 標準SMILES
CCCCCCC(=O)CCCCCC/C=C/C[C@@H](O)[C@H](O)[C@@](N)(CO)C(=O)O- InChIKey
ZZIKIHCNFWXKDY-GNTQXERDSA-N- 分子式
- C21H39NO6
- 平均分子量
- 401.5 g/mol
- 単同位体質量
- 401.27773796
概要
Myriocin is an amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity. It has a role as an antimicrobial agent, an antineoplastic agent, an immunosuppressive agent, an antifungal agent, an EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor, an apoptosis inducer and a fungal metabolite. It is a sphingoid, a hydroxy monocarboxylic acid, an alpha-amino fatty acid and a non-proteinogenic alpha-amino acid.
名称と識別子
- 優先名称
- Myriocin
- IUPAC
- (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
- 現地名
- (2S,3R,4R,6E)-2-アミノ-3,4-ジヒドロキシ-2-(ヒドロキシメチル)-14-オキソ-6-イコセン酸
- 英語名
- MYRIOCIN
- 分子式
- C21H39NO6
- 分子量
- 401.54
名称と別名
Myriocin35891-70-4thermozymocidinISP-1ISP-I(+)-MyriocinDTXSID9046360YRM4E8R9ST(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acidantibiotic ISP-I(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acidCHEBI:582124
名称をさらに表示
(+)-ミリオシンミリオシンテルモジモシジン(2S,3R,4R,6E)-2-アミノ-3,4-ジヒドロキシ-2-(ヒドロキシメチル)-14-オキソ-6-イコセン酸ミリオシン MYCELIA STERILIA(2S,3R,4R,6E)-2-アミノ-3,4-ジヒドロキシ-2-(ヒドロキシメチル)-14-オキソイコサ-6-エン酸C0019966e))-4s*NSC 177379Myriocin (ISP-1)
MYRIOCIN [MI]DTXCID70263606-Eicosenoic acid, 2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-, (2S-(2R*,3S*,4S*,6E))-6-EICOSENOIC ACID, 2-AMINO-3,4-DIHYDROXY-2-(HYDROXYMETHYL)-14-OXO-, (2S,3R,4R,6E)SPI-1 inhibitorISP-1 suppressantantibiotic ISP-1ISP-1 serine palmitoyltransferase inhibitor
物性
構造計算による物性補完中
- XLogP
- -0.1
- 極性表面積
- 141 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 7
- 回転可能結合数
- 18
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 468
実験および物理化学的性質
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]
物理化学的性質
- 融点
- 170 · 170-172℃
- 沸点
- 636.7 · 636.7±55.0 °C(Predicted)
- 比重(密度)
- 1.123 · 1.123±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 2 mg/mL · メタノール: 2 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 1.79 · 1.79±0.50(Predicted)
- 色
- オフホワイト
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 4 か月間保存できます。
- InChIKey
- ZZIKIHCNFWXKDY-XFXZXTDPSA-N
- SMILES
- N[C@]([C@@H](O)[C@H](O)C\C=C\CCCCCCC(=O)CCCCCC)(CO)C(=O)O
- CAS データベース
- 35891 · 35891-70-4
化学的性質
化学的特性White powder
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 68 reports by companies from 2 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (100%)
安全データ
- wgk
- 3
- rtecs
- JX3890000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29225090
- risk_code
- 22
- hazard_code
- Xi,Xn
- safety_code
- 24/25
- Hazard Classifications
- Acute Tox. 3 Oral
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
応用分野
説明Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus in a murine model.
使用Myriocin is a atypical amino acid and an antibiotic with potent immunosuppressant activity. Studies suggest that the immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction. Myriocin very potent inhibitor of serine palmitoyltransferase and thus blocks the synthesis ceramide, a precursor in sphingomyelin and glycosphingolipid biosynthesis. As a result Myriocin i s a useful biochemical research tool for depleting cells of sphingolipids.
一般的な説明A potent immunosuppressant. Displays 10- to 100-fold more potent immunosuppressant activity than cyclosporin A. Potently inhibits serine palmitoyltransferase (SPT; Ki = 280 pM) thereby blocking the synthesis of ceramide. Disrupts substratum adhesion of melanoma cells. Inhibits cell proliferation and induces apoptosis in IL-2 dependent murine cytotoxic T lymphocyte cell line CTLL-2.
補足説明
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