24(S),25-epoxycholesterol - Moligand™, ≥98% , Agonist of Liver X receptor-α;Agonist of Liver X receptor-β, CAS No.77058-74-3, Agonist of Liver X receptor-α;Agonist of Liver X receptor-β

CAS: 77058-74-3 Cat. No.: S491757 Molecular Weight: 400.64 PubChem CID: 3247059

GRADE & PURITY Moligand™, ≥98%

Synonyms

24(S),25-Epoxycholesterol|77058-74-3|24,25-epoxy-cholesterol|24(S), 25-epoxycholesterol|24S,25-epoxy-cholesterol|24S,25-epoxy-cholest-5-en-3beta-ol|CHEMBL434302|CHEBI:41633|(24s)-24,25-epoxycholesterol|(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimet

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

24(S),25-epoxy Cholesterol is an oxysterol and the most abundant oxysterol in mouse ventral midbrain. It activates liver X receptors (LXRs) in the developing ventral midbrain to induce stem cell differentiation into dopaminergic neurons. 24(S),25-epoxy Cholesterol inhibits IL-6 production and degranulation of bone marrow-derived murine mast cells that express LXRβ. It inhibits the conversion of desmosterol to cholesterol by 3β-hydroxysterol Δ24-reductase (DHCR24/Seladin-1) in CHO-7 and SRD-1 cells when used at a concentration of 2.5 μM

Specifications

Synonyms

24(S), 25-Epoxycholesterol | 77058-74-3 | 24, 25-epoxy-cholesterol | 24(S), 25-epoxycholesterol | 24S, 25-epoxy-cholesterol | 24S, 25-epoxy-cholest-5-en-3beta-ol | CHEMBL434302 | CHEBI:41633 | (24s)-24, 25-epoxycholesterol | (3S, 8S, 9S, 10R, 13R, 14S, 17R)-17-[(2R)-4-[(2S)-3, 3-dimet

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Endogenous cholesterol metabolite. Suppresses SREBP activation in the regulation of hepatic cholesterol metabolism in vivo .

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of Liver X receptor-α;Agonist of Liver X receptor-β

Note

Unstable; make up solutions fresh and use immediately. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(CCC1C(O1)(C)C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C
• IUPAC Name: (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• InChIKey: OSENKJZWYQXHBN-XVYZBDJZSA-N
• INCHI: 1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1
• Isomeric SMILES: C[C@H](CC[C@H]1C(O1)(C)C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C
• PubChem CID: 3247059
• Molecular Weight: 400.64

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Cholestane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Cholestane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Cholesterols and derivatives
• Alternative Parents: 3-beta-hydroxysteroids 3-beta-hydroxy delta-5-steroids Delta-5-steroids Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Epoxides Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cholesterol-skeleton - 3-hydroxy-delta-5-steroid - 3-hydroxysteroid - Hydroxysteroid - 3-beta-hydroxy-delta-5-steroid - 3-beta-hydroxysteroid - Delta-5-steroid - Cyclic alcohol - Secondary alcohol - Ether - Oxirane - Dialkyl ether - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
• External Descriptors: Cholesterol and derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

NR1H2 Tchem Oxysterols receptor LXR-beta (0 Activities)

Discover Target: NR1H2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NR1H3 Tchem Oxysterols receptor LXR-alpha (1 Activities)

Discover Target: NR1H3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NR1H3 Tchem LXR-alpha (2891 Activities)

Discover Target: NR1H3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H2 Tchem LXR-beta (3841 Activities)

Discover Target: NR1H2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 400.600 g/mol
• XLogP3: 6.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 400.334 Da
• Monoisotopic Mass: 400.334 Da
• Topological Polar Surface Area: 32.800 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 680.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1