25-Hydroxycholesterol

HCID 65094

Basic information

CAS
2140-46-7
Standard 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
Molecular formula
C27H46O2
Average molar mass
402.7 g/mol
Monoisotopic mass
402.34978071

Overview

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.

Names & identifiers

Preferred name
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
English name
25-Hydroxycholesterol
Molecular formula
C27H46O2
Molecular weight
402.65

Names & synonyms

25-Hydroxycholesterol2140-46-7Cholest-5-ene-3beta,25-diol5-Cholestene-3beta,25-diol25-OHCDTXSID5044023(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-ol767JTD2N31DTXCID3024023CHEBI:429775-cholesten-3beta,25-diolcholest-5-ene-3 beta,25-diol
Show more names
Cholest-5-ene-3β,25-diol5-Cholesten-3β,25-diolCholesterol 25-HydroxyPerampanel Impurity 395-cholestene-3β,25-diol5-CHOLESTEN-3β, 25-DIOLcholest-5-ene-3,25-diol5-CHOLESTEN-3-BETA, 25-DIOL
(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-OlRefChem:89887635-752-425-hydroxy cholesterol25-hydroxy-cholesterolMFCD00057815cholest-5-en-3beta,25-diolNCGC00181327-01

Database identifiers

CAS
2140-46-7
PubChem CID
65094
DTXSID
DTXSID5044023
ChEMBL
CHEMBL169046
ChEBI
CHEBI:42977
UNII
767JTD2N31
EC Number
635-752-4
Nikkaji
J80.397I

Properties

Computed structural properties

XLogP
6.8
Topological polar surface area
40.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
29

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section202.81 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point
177 · 177-179 °C
Boiling point
513.1 · 513.1±23.0 °C(Predicted)
Density
1.03 · 1.03±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
50 mg/mL, · chloroform: 50 mg/mL, clear, colorless to slightly yellow
pka
15.03 · 15.03±0.70(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory InformationCholest-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 CategoriesAcute Tox. 4 (100%)

Safety data

wgk
3
hs_code
29062990
risk_code
20/21/22-36/37/38-48
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn

Chemistry & industry

Applications · 4 items

Description25-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.

Uses25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.

UsesAn oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative regulation of c-Myc.

General Description25-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.

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]

Additional notes

DefinitionChEBI: 25-hydroxycholesterol is an oxysterol and a 25-hydroxy steroid. It has a role as a human metabolite. It is functionally related to a cholesterol.

Related reactions

9 records

Compound notes

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