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AB141632

24(S)-Hydroxycholesterol, Endogenous LXR agonist

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MW 402.7 Da, Purity >98%. Endogenous agonist for LXR (EC50 values are 4 μM and 3 μM at LXRα and LXRβ respectively). Involved in cholesterol homeostasis. Induces neuronal cell death by necroptosis, a form of programmed necrosis.
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Chemical Structure - 24(S)-Hydroxycholesterol, Endogenous LXR agonist (AB141632)
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Chemical Structure - 24(S)-Hydroxycholesterol, Endogenous LXR agonist (AB141632)

2D chemical structure image of ab141632, 24(S)-Hydroxycholesterol, Endogenous LXR agonist

Key facts

CAS number

474-73-7

Purity

>98%

Molecular weight

402.7 Da

Molecular formula

C<sub>2</sub><sub>7</sub>H<sub>4</sub><sub>6</sub>O<sub>2</sub>

PubChem

121948

Nature

Synthetic

Solubility

Soluble in DMSO to 25 mM

Soluble in ethanol to 25 mM (with warming)

Biochemical name

24(S)-hydroxycholesterol

Biological description

Endogenous agonist for LXR (EC50 values are 4 μM and 3 μM at LXRα and LXRβ respectively). Involved in cholesterol homeostasis. Induces neuronal cell death by necroptosis, a form of programmed necrosis.

Canonical smiles

CC(C)C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O

Isomeric smiles

C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C

InChi

InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

InChiKey

IOWMKBFJCNLRTC-XWXSNNQWSA-N

IUPAC Name

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-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

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Liver X receptor (LXR) alpha also known as NR1H3 is a nuclear receptor that plays a mechanical role in regulating gene expression related to cholesterol homeostasis and lipid metabolism. LXR alpha has an approximate mass of 51 kDa and is expressed in tissues such as the liver intestine adipose tissue and macrophages. Retinoic acid receptor-related orphan receptor (ROR) gamma also called NR1F3 functions in circadian rhythm regulation and immune response modulation. ROR gamma is expressed in various tissues including the thymus muscle and liver.
Biological function summary

LXR alpha serves as a sensor for oxysterols which are derivatives of cholesterol to maintain cholesterol and lipid homeostasis. It forms a heterodimer complex with the retinoid X receptor (RXR) to activate LXR response elements in target genes. ROR gamma is essential for the differentiation of Th17 cells critical for immune system functioning and acts as a monomer binding to ROR response elements. Both proteins are involved in regulatory networks that modulate metabolic and immune pathways.

Pathways

LXR alpha is involved in the regulation of genes such as ABCA1 and SREBP integral to cholesterol efflux and lipogenesis as part of the lipid metabolism pathway. LXR alpha also interacts with proteins like RXR. ROR gamma participates in the Th17 differentiation pathway influencing cytokine production and working alongside proteins like STAT3. Both proteins engage in balancing lipid metabolism cholesterol synthesis and immune responses ensuring proper cellular function.

LXR alpha relates to atherosclerosis and metabolic syndrome due to its role in cholesterol metabolism and lipid regulation. Disruptions cause improper lipid balance leading to these conditions. ROR gamma is significant in autoimmune diseases especially in multiple sclerosis due to its impact on Th17 cell differentiation. Changes in ROR gamma expression influence immune response and inflammation connecting it to conditions like rheumatoid arthritis. Both proteins are potential therapeutic targets for treatments related to their respective disorders.

Product protocols

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