Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H46O2 |
Molecular Weight | 402.6529 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO
InChI
InChIKey=FYHRJWMENCALJY-YSQMORBQSA-N
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
Molecular Formula | C27H46O2 |
Molecular Weight | 402.6529 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28583434Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02314208 | https://www.ncbi.nlm.nih.gov/pubmed/28739487 | https://clinicaltrials.gov/ct2/show/NCT01180361 | https://www.ncbi.nlm.nih.gov/pubmed/17873880 | https://www.ncbi.nlm.nih.gov/pubmed/15741649
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28583434
Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02314208 | https://www.ncbi.nlm.nih.gov/pubmed/28739487 | https://clinicaltrials.gov/ct2/show/NCT01180361 | https://www.ncbi.nlm.nih.gov/pubmed/17873880 | https://www.ncbi.nlm.nih.gov/pubmed/15741649
27-Hydroxycholesterol (27-HC) is an endogenous oxysterol produced by the enzyme CYP27A1, with multiple biological functions, including acting as a selective estrogen receptor modulator (SERM) and as an agonist of the liver X receptor (LXR). Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11300870 |
250.0 nM [EC50] | ||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17873880 |
|||
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17873880 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
26-Hydroxycholesterol disulfate: metabolism and excretion in the normal neonate. | 1986 Dec |
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Sterol 27-hydroxylase: expression in human arterial endothelium. | 1997 Jun |
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Activities of recombinant human cytochrome P450c27 (CYP27) which produce intermediates of alternative bile acid biosynthetic pathways. | 1998 Jul 17 |
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Oxysterol regulation of steroidogenic acute regulatory protein gene expression. Structural specificity and transcriptional and posttranscriptional actions. | 1998 Nov 13 |
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Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol. | 2000 Jun 2 |
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Immune complexes and IFN-gamma decrease cholesterol 27-hydroxylase in human arterial endothelium and macrophages. | 2001 Nov |
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Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. | 2001 Oct 19 |
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NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols. | 2003 Jul 11 |
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27-Hydroxycholesterol inhibits neutral sphingomyelinase in cultured human endothelial cells. | 2004 Aug 13 |
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Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease. | 2004 Jan |
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Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization. | 2006 May 25 |
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PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine. | 2007 Feb |
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27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen. | 2007 Oct |
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27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. | 2008 Jan |
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Glucocorticoid receptor-mediated upregulation of human CYP27A1, a potential anti-atherogenic enzyme. | 2008 Nov-Dec |
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Oxidative damage in dengue fever. | 2009 Aug 15 |
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Activity-regulated cytoskeleton-associated protein in rodent brain is down-regulated by high fat diet in vivo and by 27-hydroxycholesterol in vitro. | 2009 Jan |
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LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms. | 2009 Nov |
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Oxysterols direct B-cell migration through EBI2. | 2011 Jul 27 |
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Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein. | 2013 Mar 22 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.google.com/patents/US5773431
10 mg 27-hydroxy-cholesterol dissolved in 1.0 ml of 45% aqueous solution of 2-hydroxypropyl-β-cyclodextrin (HPBCD) was administered intravenously to one group of five test rabbits.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17873880
COS-7 cells transfected with expression plasmids for eNOS and either ER-a or ER-b were used for activity evaluation. COS-7 cells expressing ER-a or ER-b and eNOS were incubated for 15-min with 10 nM E2 or 10 nM E2+ 20mkM 27-Hydroxycholesterol (27-HC). eNOS enzymatic activity was assessed by measuring the conversion of [3H]L-arginine (Amersham) to [3H]L-citrulline.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:53:43 UTC 2023
by
admin
on
Fri Dec 15 15:53:43 UTC 2023
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Record UNII |
6T2NA6P5SQ
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C843
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6T2NA6P5SQ
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DTXSID40864941
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27-HYDROXYCHOLESTEROL
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13095-61-9
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NON-SPECIFIC STEREOCHEMISTRY | |||
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226105
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17703
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20380-11-4
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C123794
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123976
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76591
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