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트리코테신

Trichothecin

HCID 12444502
새 노트새 반응견적 요청하기인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
6379-69-7
표준 SMILES
C/C=C\C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)C(=O)C[C@]3(C)[C@]1(C)[C@]21CO1
InChIKey
LJWZOKOFCBPNAG-HULHSAFCSA-N
분자식
C19H24O5
평균 분자량
332.4 g/mol
단동위원소 질량
332.16237386

개요

Trichothecin is a trichothecene mycototoxin isolated from the endophytic fungus Trichothecium sp. and it exhibits anti-cancer properties. It has a role as a mycotoxin, an antineoplastic agent, an antifungal agent, a protein synthesis inhibitor, an apoptosis inducer and a STAT3 inhibitor.

이름 및 식별자

우선 이름
Trichothecin
IUPAC
[(1S,2R,7R,9R,11R,12S)-1,2,5-trimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-yl] (Z)-but-2-enoate
현지명
트리코테신
영어명
trichothecin
분자식
C19H24O5
분자량
332.39

이름 및 동의어

Trichothecin2GB7AS83GT6379-69-7CHEBI:69621NSC-9249212,13-Epoxy-4-hydroxytrichothec-9-en-8-one crotonateTrichothec-9-en-8-one, 12,13-epoxy-4-hydroxy-, crotonate12,13-Epoxy-4-((1-oxo-2-butenyl)oxy)trichothec-9-en-8-oneTrichothecineDTXSID30878436((1S,2R,7R,9R,11R,12S)-1,2,5-trimethyl-4-oxospiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-11-yl) (Z)-but-2-enoate[(1S,2R,7R,9R,11R,12S)-1,2,5-trimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-yl] (Z)-but-2-enoate
이름 더 보기
트리코테신Nsc924924β-Isocrotonoyloxy-12,13-epoxytrichothec-9-en-8-oneWln: T4 C5 I6 C6 A B 2cg N bo ho jutj D1 eov1U2 K1 N18-Oxo-12,13-epoxytrichothec-9-en-4β-ol (Z)-2-butenoateTrichothec-9-en-8-one,12,13-epoxy-4-[[(2Z)-1-oxo-2-butenyl]oxy]-, (4b)-Trichothec-9-en-8-one, 12,13-epoxy-4-[[(2Z)-1-oxo-2-butenyl]oxy]-, (4β)-Trichothec-9-en-8-one, 12,13-epoxy-4-[(1-oxo-2-butenyl)oxy]-, (4.beta.)-

물성

구조 계산 물성

XLogP
1.9
극성 표면적
65.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
5
회전 가능 결합 수
3
무거운 원자 수
24
형식 전하
0
복잡도
679

물리화학적 성질

녹는점
118 ° · 118°
끓는 점
389.51 °C · 389.51°C (rough estimate)
밀도
1.1165 · 1.1165 (rough estimate)
굴절률
1.612 · 1.6120 (estimate)
저장 조건
2 · 2-8°C
색상
석유 에테르에서 결정화된 가느다란 바늘 모양의 물질

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H300+H310+H330 (42.4%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 66 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 2 (100%)

독성 정보

Treatment · 1건

There are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Administer charcoal as a slurry in case of acute oral exposure. In case of inhalation: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (A704)

Health Effects · 1건

Trichothecenes have multiorgan effects including anoerxia and weight loss, growth retardation, nervous disorders, cardiovascular alterations, immunodepression, hemostatic derangements, skin toxicity, decreased reproductive capacity, bone marrow damage, and alimentary toxic aleukia. (L1948, L1949, A2964)

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Trichothecenes are lipophilic and thus easily absorbed through the skin, gut, and pulmonary mucosa. They are metabolized mainly by cytochrome P-450 and trichothecene-specific carboxylesterase activity in the liver, although other tissues such as the kidney, spleen, and intestine also show some metabolic activity. Trichothecenes are metabolically transformed to less toxic metabolites by such reactions as hydrolysis, hydroxylation, de-epoxidation, and glucuronidation. Metabolites are excreted in the urine and feces. (L1910, L1949)

용도 및 제조

Uses · 1건

Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948)

추가 설명

정의ChEBI: A natural product found in Trichothecium species MSX 51320.

공급사

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공개 문의

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관련 반응

0건
반응 기록 만들기

현재 필터 조건에 해당하는 반응 기록이 없습니다.

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
RefChem:191303DTXCID701016483(4BETA)-12,13-EPOXY-4-(((2Z)-1-OXO-2-BUTENYL)OXY)TRICHOTHEC-9-EN-8-ONEtrichothec-9-en-8-one, 12,13-epoxy-4-((1-oxo-2-butenyl)oxy)-, (4 beta)-1',2',5'-trimethyl-4'-oxo-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.02,7)dodecan)-5'-en-11'-yl but-2-enoate636-317-1NSC 92492UNII-2GB7AS83GT

데이터베이스 식별자

CAS
6379-69-7
PubChem CID
12444502
ChEMBL
CHEMBL480472
ChEBI
CHEBI:69621
UNII
2GB7AS83GT
EC Number
636-317-1
Nikkaji
J8.402F
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1건

Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. (L1948, L1949, A2962, A2963, A2964, A2980)

Signs and Symptoms · 1건

After direct dermal application or oral ingestion, the trichothecene mycotoxins can cause rapid irritation to the skin or intestinal mucosa, including skin irritation, burning and itching, rash or blisters, and bleeding. Eye contact can cause tearing, eye pain, conjunctivitis, burning sensations about the eyes, and blurred vision for up to 1 week. Symptoms also include nausea, vomiting, fatigue, dyspnea, and acute vascular effects leading to hypotension and shock. (L1948, L1949)

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

안전 데이터

rtecs
YD0175000
ridadr
3172
독성
LD50 i.v. in mice: ~300 mg/kg (Freeman)
risk_code
26/27/28-36/37/38
hazard_code
T+
safety_code
36/37/39-45
포장분류
I
위험 등급
6.1(a)