기본 정보
- CAS
17954-98-2- 표준 SMILES
CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
RZPAXNJLEKLXNO-GFKLAVDKSA-N- 분자식
- C27H46O2
- 평균 분자량
- 402.7 g/mol
- 단동위원소 질량
- 402.34978071
개요
(22R)-22-hydroxycholesterol is an oxysterol that is the 22R-hydroxy derivative of cholesterol. It is a 3beta-hydroxy-Delta(5)-steroid, a 22-hydroxy steroid and an oxysterol. It is functionally related to a cholesterol.
이름 및 식별자
- 우선 이름
- 22R-Hydroxycholesterol
- IUPAC
- (3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-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
- 영어명
- 22(R)-hydroxy Cholesterol
- 분자식
- C27H46O2
- 분자량
- 402.65
이름 및 동의어
22(R)-Hydroxycholesterol22R-hydroxycholesterol(22R)-22-Hydroxycholesterolcholest-5-en-3beta,22R-diol(3beta,22R)-Cholest-5-ene-3,22-diol(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-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-olCHEBI:67237(3S,8S,9S,10R,13S,14S,17R)-17-((2S,3R)-3-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-olRefChem:91032717954-98-222beta-Hydroxycholesterol(22R)-Hydroxycholesterol
이름 더 보기
22(R)-OH-CH22α-hydroxycholesterol22BF-HYDROXYCHOLESTEROLCholesterol 22α-Hydroxy22α-Hydroxy Cholesterol22(R)-HydroxycholesteroChlorambucil Impurity 8
22R-OHC22-alpha-Hydroxy Cholesterol22a-Hydroxy CholesterolCholest-5-ene-3,22-diol, (3beta,22R)-22alpha-Hydroxy Cholesterol(22R)-cholest-5-ene-3beta,22-diolNarthesterolCHEMBL422904
물성
구조 계산 물성
- XLogP
- 7
- 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
- 624
실험 및 물리화학적 성질
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Physical DescriptionSolid
Collision Cross Section217.74 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
물리화학적 성질
- 녹는점
- 171 · 171-174°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
- 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 15.01 · 15.01±0.20(Predicted)
- 색상
- 흰색에서 황백색까지
- InChIKey
- RZPAXNJLEKLXNO-QUOSNDFLSA-N
- SMILES
- [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)[C@H](O)CCC(C)C
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- wgk
- 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Tissue LocationsAdrenal Cortex
Cellular LocationsExtracellular
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
응용 분야
개요The liver X receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands are oxysterols. LXRs regulate the oxysterol-induced expression of cholesterol 7α-hydroxylase, the rate limiting enzyme of classic bile acid synthesis. 22(R)-hydroxy Cholesterol is an endogenous agonist for LXRs that activates LXRα with an EC50 value of 325 nM. 22(R)-hydroxy Cholesterol, acting through LXR heterodimerized with the retinoid X receptor, induces the expression of the ABCA1 reverse cholesterol transporter. This activity increases the efflux of cholesterol from enterocytes and thus inhibits the overall absorption of cholesterol. 22(R)-hydroxy Cholesterol can be used as a substrate to monitor cholesterol transport or as an endogenous positive control for testing LXR agonists which have potential as therapeutic agents for the treatment of atherosclerosis.
용도Bovine aortic endothelial cells were treated with 22(R)-Hydroxycholesterol to study the effects on production of free radicals and in studies related to fatty acid metabolism.
일반 설명22(R)-hydroxycholesterol is a diastereomer of 22(S)-hydroxycholesterol. It is present in neonate brain.
공급사44 곳
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
上海科骊科生物技术有限公司021-34975789 18721102763 · [email protected]
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