Dinophysistoxin 1
기본 정보
- CAS
81720-10-7- 표준 SMILES
C=C1[C@@H](O)[C@@H]2O[C@]3(CC[C@H](/C=C/[C@@H](C)[C@@H]4CC(C)=C[C@@]5(O[C@H](C[C@@](C)(O)C(=O)O)CC[C@H]5O)O4)O3)CC[C@H]2O[C@@H]1[C@@H](O)C[C@H](C)[C@H]1O[C@@]2(CC[C@H]1C)OCCC[C@H]2C- InChIKey
CLBIEZBAENPDFY-HNXGFDTJSA-N- 분자식
- C45H70O13
- 평균 분자량
- 819 g/mol
- 단동위원소 질량
- 818.48164228
개요
Dinophysistoxin 1 is a ketal that is a marine toxin structurally related to okadaic acid. Produced by dinoflagellates it is known to accumulate in shellfish and cause diarrhoeic shellfish poisoning. It is an inhibitor of serine/threonine protein phosphatases 1 (PP1) and PP2A and has been shown to promote cancer cell growth in tumour cell lines and animal models. It has a role as a toxin, an EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor, an animal metabolite and a marine metabolite. It is functionally related to an okadaic acid.
이름 및 식별자
- 우선 이름
- Dinophysistoxin 1
- IUPAC
- (2R)-3-[(2S,6R,8S,11R)-2-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-2-[(1S,3S)-3-[(2S,3R,6R,11R)-3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-1-hydroxybutyl]-4-hydroxy-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid
- 영어명
- 9,10-Deepithio-9,10-didehydro-35-methyl-acanthifolicin
- 분자식
- C45H70O13
- 분자량
- 819.03
이름 및 동의어
Dinophysistoxin 1Dinophysistoxin-135-Methylokadaic acidDTX1DTX 181720-10-7CHEBI:1444004Q51CVY9O2DTXSID0088000135S-methylokadaic acidDTX-1dinophytoxin-1
이름 더 보기
hDTX1hDx-1Ccris 3328Protein deltex-1DINOPHYSISTOXIN-I35-methylokadaicacid1 Dinophysistoxins 1OKADAIC ACID, 35-METHYL-
DTX-1 protein, DinophysisRefChem:588703DTXCID2010216033-(8-((3E)-4-(6'-(3-(3,11-dimethyl-1,7-dioxaspiro(5.5)undecan-2-yl)-1-hydroxybutyl)-8'-hydroxy-7'-methylidene-hexahydro-3'H-spiro(oxolane-2,2'-pyrano(3,2-b)pyran)-5-yl)but-3-en-2-yl)-5-hydroxy-10-methyl-1,7-dioxaspiro(5.5)undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid(2R)-3-((2R,8S,11R)-2-((E,2R)-4-((2S,2'R,4R,4aS,6R,8aR)-2-((1S,3S)-3-((2S,3R,6R,11R)-3,11-dimethyl-1,7-dioxaspiro(5.5)undecan-2-yl)-1-hydroxybutyl)-4-hydroxy-3-methylidenespiro(4a,7,8,8a-tetrahydro-4H-pyrano(3,2-b)pyran-6,5'-oxolane)-2'-yl)but-3-en-2-yl)-11-hydroxy-4-methyl-1,7-dioxaspiro(5.5)undec-4-en-8-yl)-2-hydroxy-2-methylpropanoic acid(2R)-3-((2S,6R,8S,11R)-2-((E,2R)-4-((2S,2'R,4R,4aS,6R,8aR)-2-((1S,3S)-3-((2S,3R,6R,11R)-3,11-dimethyl-1,7-dioxaspiro(5.5)undecan-2-yl)-1-hydroxybutyl)-4-hydroxy-3-methylidenespiro(4a,7,8,8a-tetrahydro-4H-pyrano(3,2-b)pyran-6,5'-oxolane)-2'-yl)but-3-en-2-yl)-11-hydroxy-4-methyl-1,7-dioxaspiro(5.5)undec-4-en-8-yl)-2-hydroxy-2-methylpropanoic acid(2R)-3-((2S,6R,8S,11R)-2-((E,2R)-4-((2S,2'R,4R,4aS,6R,8aR)-2-((1S,3S)-3-((3R,6R,11R)-3,11-dimethyl-1,7-dioxaspiro(5.5)undecan-2-yl)-1-hydroxybutyl)-4-hydroxy-3-methylidenespiro(4a,7,8,8a-tetrahydro-4H-pyrano(3,2-b)pyran-6,5'-oxolane)-2'-yl)but-3-en-2-yl)-11-hydroxy-4-methyl-1,7-dioxaspiro(5.5)undec-4-en-8-yl)-2-hydroxy-2-methylpropanoic acid620-510-2
물성
구조 계산 물성
- XLogP
- 3.8
- 극성 표면적
- 183 Ų
- 수소 결합 공여자 수
- 5
- 수소 결합 수용자 수
- 13
- 회전 가능 결합 수
- 10
- 무거운 원자 수
- 58
- 형식 전하
- 0
- 복잡도
- 1,550
물리화학적 성질
- 녹는점
- 134 °C · 134 °C
- 끓는 점
- 679.27 °C · 679.27°C (rough estimate)
- 밀도
- 1.0717 · 1.0717 (rough estimate)
- 굴절률
- 1.594 · 1.5940 (estimate)
- 저장 조건
- -20 °C · -20°C
- 용해도
- DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 3.87 · 3.87±0.16(Predicted)
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, 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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesAcute Tox. 3 (97.5%)
독성 정보
TreatmentAn antivenom exists for Black mamba venom. (L1044)
Health EffectsDendrotoxins and neurotoxic. (L1096)
Exposure Routes
Injection (sting/bite) (L1814)
Ingestion
Toxicity Summary
Dendrotoxins block particular subtypes of voltage-gated potassium channels in neurons, thereby prolonging the duration of action potentials and enhancing the release of acetylcholine at neuromuscular junctions, which may result in muscle hyperexcitability and convulsive symptoms. This is believed to be done by binding to anionic sites near the extracellular surface of the channel and physically occluding the pore, thereby preventing ion conductance. (L1096)
Dinophysistoxin 1 (DTX1) is the analogue of okadaic acid causing diarrheic shellfish poisoning (DSP) in humans shortly after the ingestion of contaminated seafood. DTX1 is able to disrupt the integrity of Caco-2 monolayer cells at concentrations above 50 nM. In addition, confocal microscopy imaging confirmed that the tight-junction protein, occludin, was affected by DTX1. Permeability assays revealed that only DTX1 was able to significantly cross the intestinal epithelium at concentrations above 100 nM. The mechanism of action of this group of toxins is mainly the potent inhibition of serine/threonine protein phosphatases 1 (PP1) and 2A (PP2A). DTX1-treated Caco-2 monolayers could damage tight-junctions among cells. Tight-junctions form the physical barrier to the diffusion of substances through the paracellular space.
화학 및 산업
약리 정보
Metabolism/Metabolites
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.
용도 및 제조
Uses
Dendrotoxin-1 is a peptide toxin produced by the Black mamba (Dendroaspis polylepis polylepis). (L1096)
Dinophysistoxin 1 is found in mollusks. Dinophysistoxin 1 is a metabolite of Dinophysis fortii. Dinophysistoxin 1 is found in scallops and mussels. Component toxin in diarrhetic shellfish poisoning. Dinophysistoxin 1 belongs to the family of Okadaic Acids and Derivatives.
응용 분야
용도Dinophysistoxin-1 is a lipophilic toxin produced by marine dinoflagellates that can accumulate in shellfish and cause diarrhetic shellfish poisoning. DTX1. EU regulated marine toxin.
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