기본 정보
- 표준 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- 분자식
- C27H46O2
- 평균 분자량
- 402.7 g/mol
- 단동위원소 질량
- 402.34978071
개요
25-hydroxycholesterol is a 25-hydroxy steroid and an oxysterol. It has a role as a human metabolite. It is functionally related to a cholesterol.
이름 및 식별자
- 우선 이름
- 25-Hydroxycholesterol
- IUPAC
- (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- 현지명
- 25-하이드록시콜레스테롤
- 영어명
- 25-Hydroxycholesterol
- 분자식
- C27H46O2
- 분자량
- 402.65
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
2140-46-7- PubChem CID
- 65094
- DTXSID
DTXSID5044023- ChEMBL
CHEMBL169046- ChEBI
CHEBI:42977- UNII
- 767JTD2N31
- EC Number
- 635-752-4
- Nikkaji
- J80.397I
물성
구조 계산 물성
- XLogP
- 6.8
- 극성 표면적
- 40.5 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 636
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- 177 · 177-179 °C
- 끓는 점
- 513.1 · 513.1±23.0 °C(Predicted)
- 밀도
- 1.03 · 1.03±0.1 g/cm3(Predicted)
- 저장 조건
- -20 °C · -20°C
- 용해도
- 50 mg/mL, · 클로로포름: 50mg/mL, 투명, 무색 내지 약간 노란색
- 산도 계수 (pKa)
- 15.03 · 15.03±0.70(Predicted)
- 물리적 상태
- 고체
- 색상
- 흰색 또는 연한 노란색
- 생물학적 소스
- synthetic (organic)
- Merck
- 13 · 13,4846
- BRN
- 3161259 · 3161259
- 안정성
- 1 · 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
GHS Classification
Warning
H302 (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.
유해성 정보
안전 데이터
- wgk
- 3
- HS 번호
- 29062990
- risk_code
- 20/21/22-36/37/38-48
- hazard_code
- Xn
- safety_code
- 26-36-45
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
응용 분야
개요25-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.
용도25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.
일반 설명25-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.
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