(25R)-26-Hydroxycholesterol
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(25R)-26-Hydroxycholesterol
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CAS No:
20380-11-4
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Formula:
C27H46O2
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Chemical Name:
(25R)-26-Hydroxycholesterol
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Synonyms:
Cholest-5-ene-3,26-diol,(3β,25R)-;Cholest-5-ene-3β,26-diol,(25R)-;(3β,25R)-Cholest-5-ene-3,26-diol;(25R)-Cholest-5-ene-3β,26-diol;(25R)-26-Hydroxycholesterol;(3β,25R)-Cholest-5-ene-3,26-diol
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CAS No:
Description
Solid
(25R)-cholest-5-ene-3beta,26-diol is a 26-hydroxycholesterol in which the 25-position has R-configuration. It has a role as an apoptosis inducer, a neuroprotective agent, a human metabolite and a mouse metabolite. It derives from a cholesterol.|27-Hydroxycholesterol is an endogenous metabolite of cholesterol produced by the hydroxylation of the carbon at position 27 by the enzyme sterol 26-hydroxylase, mitochondrial (CYP27A1). Some neoplasms produce excess of 27-hydroxycholesterol (27HC) or inhibit its catabolism, and high cholesterol levels are correlated with elevated levels of 27HC; under these conditions, 27HC may have deleterious selective estrogen receptor modulator (SERM) and liver X receptor (LXR) agonistic activities. As a SERM, 27HC binds to and prevents the activation of estrogen receptors (ERs) in the vasculature. This prevents ER-mediated vasodilation and abrogates the cardiovascular protective effects of estrogen. However, 27HC binds to and activates ERs and LXRs in breast tissue, which stimulates ER-dependent breast cancer cell growth and metastasis.
Characteristics
40.46000
6.36110
1.03
172-174 °C @ Solvent: Hexane, Ethyl acetate
517.1ºC at 760 mmHg
215.6ºC
1.537
7.43E-13mmHg at 25°C
(25R)-26-Hydroxycholesterol Use and Manufacturing
Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Computed Properties
Molecular Weight:402.7
XLogP3:7.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:402.349780706
Monoisotopic Mass:402.349780706
Topological Polar Surface Area:40.5
Heavy Atom Count:29
Complexity:612
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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