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N-(2-キノキサリニルカルボニル)シクロ(D-Ser*-Ala-N-メチル-L-Cys(1)-N-メチル-L-Val-N-(キノキサリン-2-イルカルボニル)-D-Ser*-Ala-N-メチル-3-メチルチオ-L-Ala(1)-N-メチル-L-Val-)

Echinomycin

HCID 6857732
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基本情報

CAS
512-64-1
標準SMILES
CSC1SC[C@H]2C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c3cnc4ccccc4n3)C(=O)N[C@@H](C)C(=O)N(C)[C@@H]1C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c1cnc3ccccc3n1)C(=O)N[C@@H](C)C(=O)N2C
InChIKey
AUJXLBOHYWTPFV-VITLIGDRSA-N
分子式
C51H64N12O12S2
平均分子量
1,101.3 g/mol
単同位体質量
1,100.42080787

概要

Echinomycin is a cytotoxic polypeptide quinoxaline antibiotic isolated from Streptomyces echinatus that binds to DNA and inhibits RNA synthesis.

名称と識別子

優先名称
Echinomycin
IUPAC
N-[(1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamide
現地名
N-(2-キノキサリニルカルボニル)シクロ(D-Ser*-Ala-N-メチル-L-Cys(1)-N-メチル-L-Val-N-(キノキサリン-2-イルカルボニル)-D-Ser*-Ala-N-メチル-3-メチルチオ-L-Ala(1)-N-メチル-L-Val-)
英語名
QUINOMYCIN A
分子式
C51H64N12O12S2
分子量
1101.26

名称と別名

EchinomycinQuinomycin A512-64-1NSC-526417TG824J6RQTNSC 526417SK 302BSK-302BANTIBIOTIC A-654IBRN 0078671NSC526417NSC-13502
名称をさらに表示
N-(2-キノキサリニルカルボニル)シクロ(D-Ser*-Ala-N-メチル-L-Cys(1)-N-メチル-L-Val-N-(キノキサリン-2-イルカルボニル)-D-Ser*-Ala-N-メチル-3-メチルチオ-L-Ala(1)-N-メチル-L-Val-)エキノマイシンキノマイシンAN-[(1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-ヘキサメチル-27-(メチルスルファニル)-3,6,10,13,16,19,23,26-オクタオキソ-11,24-ビス(プロパン-2-イル)-20-(キノキサリン-2-アミド)-9,22-ジオキサ-28-チア-2,5,12,15,18,25-ヘキサアザビシクロ[12.12.3]ノナコサン-7-イル]キノキサリン-2-カルボキサミドNSC 13502echinomycinaEchinomycin >97%Antibiotic A 654IEchinomycin (NSC-13502)Echinomycin, HIF-1alpha inhibitor
Echinomycin ADTXSID5031266N-((1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo(12.12.3)nonacosan-7-yl)quinoxaline-2-carboxamideN-[(1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamideBis-Quinoline AnalogueRefChem:136231DTXCID3011266N-(2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo(12.12.3)nonacosan-7-yl)quinoxaline-2-carboxamide

データベース識別子

CAS
512-64-1
PubChem CID
6857732
ChEMBL
CHEMBL503868、CHEMBL510650
UNII
TG824J6RQT
EC Number
637-095-9
Nikkaji
J34.323D

物性

構造計算による物性

XLogP
2.7
極性表面積
352 Ų
水素結合供与体数
4
水素結合受容体数
18
回転可能結合数
7
重原子数
77
形式電荷
0
複雑度
2,200

実験および物理化学的性質

SolubilitySoluble in 5% Cremophor EL /5% ethanol /90% water at 0.4mg/mL. Very insoluble in water.
Optical Rotation(c = 1.10, chloroform) [a]23D = -321 ± 2°
Stability/Shelf LifeBulk: Should be stored at 5 °C or less.

物理化学的性質

融点
217 · 217-218℃
比旋光度
20 · D20 -310° (c = 0.86 in chloroform)
沸点
1427.2 · 1427.2±65.0 °C(Predicted)
比重(密度)
1.0964 · 1.0964 (rough estimate)
屈折率
1.67 · 1.6700 (estimate)
貯蔵温度
-20 °C · -20°C
溶解性
DMSO に可溶 (5 mg/ml まで)
酸解離定数(Pka)
9.38 · 9.38±0.70(Predicted)
外見
白い固体
色
白からベージュ
Merck
13 · 13,3531
安定性
-20 °C · -20°C の DMSO 溶液で最大 3 か月間保存できます。
InChIKey
AUJXLBOHYWTPFV-UHFFFAOYSA-N
SMILES
S1C(C2N(C(=O)C(NC(=O)C(COC(=O)C(N(C(=O)C(N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5nc6c(nc5)cccc6)C)C)C1)C)C(C)C)NC(=O)c3nc4c(nc3)cccc4)C)C)SC

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 · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Toxicity Data · 4 件

Mouse(ip): LD50: 400 µg/kg

Mouse(sc): LD50: 3800 µg/kg

Mouse(iv): LD50: 629 µg/kg

Dog(iv): LD Lo: 89 µg/kg

安全データ

F
10
wgk
3
rtecs
JW5250000
ridadr
UN 3462 6.1/PG 2
hs_code
2941900000
risk_code
46-23/24/25
hazard_code
T
safety_code
53-36/37/39-45
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralRepr. 2
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 · 3 件

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.

Compounds that inhibit cell production of DNA or RNA.

Substances that inhibit the growth or reproduction of BACTERIA.

応用分野 · 2 件

説明Hypoxia-inducible factor-1 (HIF-1) is a transcription factor that controls genes involved in glycolysis, angiogenesis, migration, and invasion. Echinomycin is a cell-permeable inhibitor of HIF-1-mediated gene transcription. It acts by intercalating into DNA in a sequence-specific manner, blocking the binding of either HIF-1α or HIF-1β to the hypoxia-responsive element. Echinomycin reversibly inhibits hypoxia-induced HIF-1 transcription activity in U215 cells with an EC50 value of 1.2 nM. It inhibits hypoxia-induced expression of vascular endothelial growth factor, blocking angiogenesis and altering excitatory synaptic transmission in hippocampal neurons. Echinomycin also impairs expression of survivin, enhancing the sensitivity of multiple myeloma cells to melphalan.

使用Quiniomycin A is a cyclic depsipeptide metabolite. Quinomycin A has broad activity against bacteria, fungi and viruses, and has found application as an antitumour agent. Quinomycin A acts by bifunctional intercalation of nucleic acids. Recent research has shown quinomycin A to be an extremely potent inhibitor of hypoxia-inducible factor-1 (HIF-1). This transcription factor plays an essential role in tumour progression and metastasis.

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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート