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Gliotoxin

HCID 6223
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
67-99-2
표준 SMILES
CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3
InChIKey
FIVPIPIDMRVLAY-RBJBARPLSA-N
분자식
C13H14N2O4S2
평균 분자량
326.4 g/mol
단동위원소 질량
326.03949928

개요

Gliotoxin is a pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. It has a role as a mycotoxin, an immunosuppressive agent, an antifungal agent, a proteasome inhibitor and an EC 2.5.1.58 (protein farnesyltransferase) inhibitor. It is an organic disulfide, an organic heterotetracyclic compound, a dipeptide and a pyrazinoindole.

이름 및 식별자

우선 이름
Gliotoxin
IUPAC
(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione
영어명
GLIOTOXIN
분자식
C13H14N2O4S2
분자량
326.39

이름 및 동의어

gliotoxin67-99-2AspergillinDTXSID608771795L648PH06KCHEBI:5385NSC-10286610H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-GliotoxinsS. N.-12870(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dioneNSC102866
이름 더 보기
S-82s.n.12870Aids086418Aids-086418Gliotoxin solutionAspergillin solutionGliotoxin in Acetonitrile
(3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione10H-3,10A-EPIDITHIOPYRAZINO(1,2-A)INDOLE-1,4-DIONE, 2,3,5A,6-TETRAHYDRO-6-HYDROXY-3-(HYDROXYMETHYL)-2-METHYL-, (3R,5AS,6S,10AR)-(3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino(1,2-a)indole-1,4-dione(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino(1,2-a)indole-1,4-dioneRefChem:143379DTXCID7010152617-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo(9.2.2.01,9.03,8)pentadeca-3,5-diene-10,14-dioneGliotoxin from Gliocladium fimbriatum

물성

구조 계산 물성

XLogP
-0.7
극성 표면적
132 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
6
회전 가능 결합 수
1
무거운 원자 수
21
형식 전하
0
복잡도
621

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Antibiotics

물리화학적 성질

녹는점
221 °C · 221°C (rough estimate)
끓는 점
699.7 · 699.7±55.0 °C(Predicted)
밀도
1.4069 · 1.4069 (rough estimate)
굴절률
1.651 · 1.6510 (estimate)
인화점
2 ℃ · 2℃
저장 조건
2 · 2-8°C
용해도
10 mg/mL, · 클로로포름: 10mg/mL, 투명, 무색
물리적 상태
흰색 고체
산도 계수 (pKa)
12.9 · 12.90±0.40(Predicted)
색상
MeOH 로부터 단사 결정체를 얻는다
Merck
13 · 13,4454
BRN
50675 · 50675
안정성
2 · 공급된 대로 2년 동안 안정적입니다. DMSO의 솔루션은 -20°C에서 최대 1개월 동안 보관할 수 있습니다.
InChI
InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
InChIKey
FIVPIPIDMRVLAY-RBJBARPLSA-N

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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 42 reports by companies from 1 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory Information10H-3,10a-Epidithiopyrazino1,2-aindole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-, (3R,5aS,6S,10aR)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (100%)

독성 정보

Health EffectsGliotoxin has immunosuppressive effects. It is also cytotoxic and causes neurite degeneration. (L1941, A2951)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1건

Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. It also acts as an inhibitor of farnesyl transferase. Gliotoxin noncompetitively inhibits the chymotrypsin-like activity of the 20S proteasome and displays anti-inflammatory activity. It acts by blocking thiol groups in the cell membranes. Gliotoxin is also cytotoxic and causes neurite degeneration. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (L1941, A2951, A3014)

화학 및 산업

약리 정보

MeSH Pharmacological Classification · 1건

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.

용도 및 제조

Uses · 1건

Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Gliotoxin possesses immunosuppressive properties. (L1941)

응용 분야 · 1건

용도Gliotoxin is a sulfur-containing mycotoxin produced by species of fungi and pathogens of humans. Gliotoxin exhibits inhibitory activities against histone H3K9 methyltransferase, a key enzyme in the re gulation of transcriptional activity by writing epigenetic marks. Gliotoxin also exhibits immunosuppressive properties by causing apoptosis of cells of the immune system. In addition, various studies suggests Gliotoxin may also be a potential anti-inflammatory, antibiotic, antifungal and antiviral agent.

상·하류 제품 정보

하류 제품

(3R)-2,3,5aβ,6α-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epitetrathiopyrazino[1,2-a]indole-1,4-dioneBIS(METHYLTHIO)글리오톡신

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
67-99-2
PubChem CID
6223
DTXSID
DTXSID60877179
ChEMBL
CHEMBL331627
ChEBI
CHEBI:5385
UNII
5L648PH06K
EC Number
636-170-3
Nikkaji
J9.768C
SMILES
N12C(=O)[C@@]3(CO)SS[C@@]1(C(=O)N3C)CC1[C@@]2([H])[C@@H](O)C=CC=1

화학적 성질

White powder

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

안전 데이터

wgk
3
rtecs
KB4725000
ridadr
UN 3462 6.1/PG 3
독성
LD50 oral in mouse: 67mg/kg
HS 번호
29419090
risk_code
25-36-20/21/22-11
hazard_code
T,Xn,F
safety_code
36/37/39-45-36/37-16
포장분류
III
위험 등급
6.1(b)
F 고인화성물질
4.2-10-23
Hazard Classifications
Acute Tox. 3 Oral
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

공급사83 곳

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추가 설명

정의ChEBI: A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.