25-하이드록시콜레스테롤

25-하이드록시콜레스테롤 · Cholest-5-ene-3β,25-diol · 25-Hydroxycholesterol · 5-Cholesten-3β,25-diol · Cholesterol 25-Hydroxy · Perampanel Impurity 39 · 5-cholestene-3β,25-diol · 5-CHOLESTEN-3β, 25-DIOL

https://huagongshe.com/ko/chemical/65094

식별자 및 물리적 특성

CAS No.	2140-46-7
분자식	C27H46O2
평균 분자량	402.7 g/mol
단동위원소 질량	402.34978071 g/mol
SMILES	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey	INBGSXNNRGWLJU-ZHHJOTBYSA-N
PubChem CID	65094
ChEMBL	CHEMBL169046
ChEBI	CHEBI:42977
EC No.	635-752-4
DTXSID	DTXSID5044023
현지명	25-하이드록시콜레스테롤

화학 및 물리적 성질

XLogP	6.8
극성 표면적	40.5
수소 결합 공여자 수	2
수소 결합 수용자 수	2
회전 가능 결합 수	5
무거운 원자 수	29
형식 전하	0
복잡도	636
의약품	Pharmaceuticals -> Listed in ZINC15
지질	Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Endocrine Disruptors	Potential endocrine disrupting compound
Collision Cross Section	202.81 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]
녹는점	177-179 °C
끓는 점	513.1±23.0 °C(Predicted)
밀도	1.03±0.1 g/cm3(Predicted)
저장 조건	-20°C
용해도	클로로포름: 50mg/mL, 투명, 무색 내지 약간 노란색
pKa(산도 계수)	15.03±0.70(Predicted)
물리적 상태	고체
색상	흰색 또는 연한 노란색
생물학적 소스	synthetic (organic)
Merck	13,4846
BRN	3161259
안정성	제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°에서 최대 3개월 동안 보관할 수 있습니다.
InChIKey	INBGSXNNRGWLJU-ZHHJOTBYSA-N
SMILES	[C@@]12([H])CC[C@H]([C@H](C)CCCC(O)(C)C)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21[H] \|&1:0,4,5,14,18,20,24,30,r\|

화학적 성질

Off-White Solid

안전 및 규제

GHS 분류	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Cholest-5-ene-3,25-diol, (3.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories	Acute Tox. 4 (100%)
수질 위해 등급(WGK)	3
관세 코드	29062990
위험 문구(R)	20/21/22-36/37/38-48
위험 표시	Xn
안전 문구(S)	26-36-45
저장 분류	11 - Combustible Solids

용도

개요

25-hydroxy Cholesterol is an oxysterol. It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection. 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM). 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 3.675 μM) and reduces increases in viral protein production in infected Vero cells when used prior to infection. It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in mice expressing human angiotensin-converting enzyme 2 (hACE2), the functional receptor for SARS-CoV-2, in a model of SARS-CoV-2 infection and in a patient with COVID-19, the primarily respiratory disease caused by SARS-CoV-2.

용도

25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.

일반 설명

25-hydroxy-cholesterol is a side chain substituted oxysterol. Avanti′s unique sterol reverses cataracts in mice. Gestwicki′s team ...... settled on compound 29, a steroid found naturally in the bloodstream but not in the lens, which has no blood supply. Mice with age-related and hereditary cataracts received drops in the right eye, whereas the left eye went untreated. After just a few weeks, the treated eye was visibly clearer, says Gestwicki, who conducted the work while at the University of Michigan. Cataract severity is measured on a scale of zero to four, with four being the worst case. On average, mice in the study had about a one-grade improvement in cataract severity after 4 weeks of treatment. Science DOI: 10.1126/science.aad7400 It has been recently shown that activation of a macrophage toll-like receptor (TLR) by microbial antigens induces synthesis of 25-hydroxycholesterol, and that this oxysterol potently suppresses IgA production.