25-Hydroxycholesterol

HCID 65094CAS 2140-46-7

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Grundinformationen

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
Summenformel: C27H46O2
Durchschnittliche Molmasse: 402,7 g/mol
Monoisotopische Masse: 402,34978071

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Englischer Name: 25-Hydroxycholesterol
Summenformel: C27H46O2
Molmasse: 402.65

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 6,8
Polarare Oberfläche (TPSA): 40,5 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 5
Schwere Atome: 29
Formalladung: 0
Komplexität: 636

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section202.81 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physikochemische Eigenschaften

Schmelzpunkt: 177 · 177-179 °C
Siedepunkt: 513.1 · 513.1±23.0 °C(Predicted)
Dichte: 1.03 · 1.03±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
Löslichkeit: 50 mg/mL, · chloroform: 50 mg/mL, clear, colorless to slightly yellow
pka: 15.03 · 15.03±0.70(Predicted)
Aggregatzustand: solid
Farbe: White or pale yellow
Biologische Quelle: synthetic (organic)
Merck: 13 · 13,4846
BRN: 3161259 · 3161259
Stabilität: 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
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|

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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%)

Sicherheitsdaten

wgk: 3
hs_code: 29062990
risk_code: 20/21/22-36/37/38-48
hazard_code: Xn
safety_code: 26-36-45
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

Beschreibung25-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.

Verwenden25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.