Oxysterols derived from cholesterol (Homo sapiens)
From WikiPathways
Description
The Oxysterol group of compounds are oxygenated derivatives of cholesterol or its sterol precursors, e.g. 7-dehydrocholesterol (7-DHC) or desmosterol. There are three mechanisms leading to the formation of oxysterols: 1) Enzymatically (first steps of sterol metabolism, being intermediates for the formation of steroid hormones, bile acids and 1,25-dihydroxyvitamin D3), 2) Non-enzymatically by encountering reactive oxygen species (ROS), providing a second pool of metabolites (this pool also includes oxidized cholesterol molecules taken in from diet), see https://www.wikipathways.org/instance/WP5064, and 3) Generation by the gut microflora and uptake through the enterohepatic circulation.
Previously oxysterols where though to be inactive metabolic intermediates, however recent findings have established that these metabolites are involved in cholesterol homoeostasis, can be ligands to nuclear and G protein-coupled receptors and biomarkers of diseases (for example Niemann-Pick disease).
This pathway drawing was inspired by Figure 3 of the review article by Griffiths et al. 2016, and has been extended with immune system, receptor agonists, steroidal alkaloid and biomarker information from the same paper. This pathway has been updated with Figure 1 from Griffiths et al. 2020 (green areas), Figure 2 (yellow area) and Figure 3 (blue area).Quality Tags
Ontology Terms
Bibliography
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History
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External references
DataNodes
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Name | Type | Database reference | Comment |
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7α,25-Dihydroxycholesterol | Metabolite | LMST04030166 (LIPID MAPS) |
|
7α-Hydroxy-3-oxocholest-4-en -(25R)26-oyl-CoA | Metabolite | LMST04030252 (LIPID MAPS) | aka 7α-Hydroxy-3-oxocholest-4-en-(25R)26-oyl-CoA |
(25R)26-Hydroxycholesterol | Metabolite | LMST01010088 (LIPID MAPS) |
|
24S-Hydroxycholesterol | Metabolite | LMST01010019 (LIPID MAPS) |
|
24S-hydroxycholesterol | Metabolite | LMST01010019 (LIPID MAPS) |
|
25-Hydroxycholesterol | Metabolite | LMST01010018 (LIPID MAPS) |
|
26-Hydroxy-7-oxocholesterol | Metabolite | LMST04030180 (LIPID MAPS) | |
3beta-Sulfooxy-7beta-N-acetylglucosaminyl chol-5-en-24-oic acid | Metabolite | LMST04010468 (LIPID MAPS) | |
3beta-hydroxy-7beta-N-acetylglucosaminyl chol-5-en-24-oylglycine | Metabolite | LMST04010471 (LIPID MAPS) | |
3beta-hydroxy-7beta-N-acetylglucosaminyl chol-5-en-24-oyltaurine | Metabolite | LMST04010472 (LIPID MAPS) | |
3α,7α,12α−Trihydroxy-5β-cholestan -(25R)26-oic acid | Metabolite | LMST04030151 (LIPID MAPS) | AKA (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid |
3β,5α-Dihydroxycholestan-6-one | Metabolite | LMST01010126 (LIPID MAPS) | |
3β,7α-Dihydroxycholest
-5-en-(25R)26-oic acid | Metabolite | LMST04030241 (LIPID MAPS) | Aka 3β,7α-dihydroxycholest-5-en-(25R)26-oic acid |
3β,7β-Dihydroxychol-5-en-24-oic acid | Metabolite | LMST04010218 (LIPID MAPS) | |
3β,7β-Dihydroxycholest-5-en(25R)26-oic acid | Metabolite | LMST04030235 (LIPID MAPS) | |
3β-Hydroxy-7-oxochol-5-en- 24-oic acid | Metabolite | LMST04010394 (LIPID MAPS) | |
3β-Hydroxy-7-oxocholest-5-en- (25R)26-oic acid | Metabolite | LMST04030239 (LIPID MAPS) | |
3β-Hydroxycholest
-5-en-(25R)-26-oic acid | Metabolite | LMST04030072 (LIPID MAPS) |
|
5,6-epoxycholesterol sulfate | Metabolite | LMST05020067 (LIPID MAPS) | |
5α,6α-Epoxycholesterol | Metabolite | LMST01010011 (LIPID MAPS) | AKA 5,6α-epoxycholesterol |
5β-Cholestane-
3α,7α,12α,(25R)26- tetrol | Metabolite | LMST04030160 (LIPID MAPS) | aka (25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetrol |
5β-Cholestane-3α,7α,12α−triol | Metabolite | LMST04030035 (LIPID MAPS) | aka 5beta-cholestane-3alpha,7alpha,12alpha-triol ; trihydroxycoprostane |
7-Dehydrocholesterol | Metabolite | LMST01010069 (LIPID MAPS) | |
7-Oxocholesterol and 7β-Hydroxycholesterol pathways | Pathway | WP5064 (WikiPathways) | |
7-Oxocholesterol | Metabolite | LMST01010049 (LIPID MAPS) | |
7α(25S)26- Dihydroxycholesterol | Metabolite | LMST01010466 (LIPID MAPS) | aka 7α,(25S)26-dihydroxycholesterol |
7α(25S)26-Dihydroxycholest -4-en-3-one | Metabolite | LMST01010465 (LIPID MAPS) | aka 7α,(25S)26-dihydroxycholest-4-en-3-one |
7α, 12α,(25R)26−
Trihydroxycholest -4-en-3-one | Metabolite | LMST01010464 (LIPID MAPS) | aka 7alpha,12alpha,(25R)26-trihydroxycholest-4-en-3-one |
7α,(25R)26-Dihydroxycholesterol | Metabolite | LMST01010462 (LIPID MAPS) | AKA 7α,26-dihydroxycholesterol; 7-alpha, (25R)26-diHC |
7α,(25R)26−Dihydroxycholest -4-en-3-one | Metabolite | LMST01010463 (LIPID MAPS) | aka (25R)-7alpha,26-dihydroxycholest-4-en-3-one |
7α,12α,(25R)26-
Trihydroxy-5β- cholestan-3-one | Metabolite | LMST04030246 (LIPID MAPS) | aka 7α,12α,(25R)26-TriHydroxy-5β-cholestan-3-one |
7α,12α,24,25-Tetrahydroxycholest -4-en-3-one | Metabolite | LMST04030248 (LIPID MAPS) | aka 7α,12α,24,25-Tetrahydroxycholest-4-en-3-one |
7α,12α,25-Trihydroxycholest -4-en-3,24-dione | Metabolite | LMST04030249 (LIPID MAPS) | aka 7α,12α,25-Trihydroxycholest-4-en-3,24-dione |
7α,12α,25-Trihydroxycholest -4-en-3-one | Metabolite | LMST04030105 (LIPID MAPS) | aka 7α,12α,25-Trihydroxycholest-4-en-3-one |
7α,12α-Dihydroxy
-3-oxocholest-4-en- (25R)26-oic acid | Metabolite | LMST04030243 (LIPID MAPS) | aka 7-alpha,12-alpha-diHydroxy-3-oxocholest-4-en-(25R)26-oic acid (not available in Wikidata) |
7α,12α-Dihydroxy-3-oxo-5β- cholestan-(25R)26-oic acid | Metabolite | LMST04030245 (LIPID MAPS) | aka 7α,12α-diHydroxy-3-oxo-5β-cholestan-(25R)26-oic acid |
7α,12α-Dihydroxy-3-oxochol-4-en-24-oic | Metabolite | LMST04010241 (LIPID MAPS) | aka 7a,12a-Dihydroxy-3-oxochol-4-en-24-oic acid |
7α,12α−Dihydroxy-5β-cholestan -3-one | Metabolite | LMST04030113 (LIPID MAPS) | aka 7alpha,12alpha-dihydroxy-5beta-cholestan-3-one |
7α,12α−Dihydroxycholest -4-en-3-one | Metabolite | LMST04030114 (LIPID MAPS) | aka 7alpha-hydroxycholest-4-en-3-one |
7α,24R-Dihydroxy-3-oxocholest- 4-en-(25R)26-oyl-CoA | Metabolite | LMST04030256 (LIPID MAPS) | |
7α,24S-Dihydroxy-3-oxocholest -4-en-(25R)26-oic acid | Metabolite | LMST04030247 (LIPID MAPS) |
|
7α,24S-Dihydroxy-3-oxocholest- 4-en-(25R)26-oic acid | Metabolite | LMST04030247 (LIPID MAPS) | |
7α,24S-Dihydroxy-3-oxocholest- 4-en-(25R)26-oyl CoA | Metabolite | LMST04030251 (LIPID MAPS) | |
7α,24S-Dihydroxycholest -4-en-3-one | Metabolite | LMST04030216 (LIPID MAPS) | aka 7α,24S-Dihydroxycholest-4-en-3-one |
7α,24S-Dihydroxycholesterol, | Metabolite | LMST04030168 (LIPID MAPS) |
|
7α,25-Dihydroxy-3-oxocholest -4-en-26-oic acid | Metabolite | LMST04030263 (LIPID MAPS) |
|
7α,25-Dihydroxycholest -4-en-3-one | Metabolite | LMST04030107 (LIPID MAPS) | aka 7α,25-Dihydroxycholest-4-en-3-one, 7a,25-diHCO. |
7α,25-Dihydroxycholesterol | Metabolite | LMST04030166 (LIPID MAPS) |
|
7α-Hydroxy-3,24-bisoxocholest-4- en-(25R)26-oyl-CoA | Metabolite | LMST04030254 (LIPID MAPS) | |
7α-Hydroxy-3-
oxocholest-4-en- (25R)26-oic acid | Metabolite | LMST04030242 (LIPID MAPS) | aka 7-Hydroxy-3-oxocholest-4-en-(25R)26-oic acid |
7α-Hydroxy-3-oxochol- 4-en-24-oic acid | Metabolite | LMST04010239 (LIPID MAPS) | |
7α-Hydroxy-3-oxochol- 4-en-24-oyl-CoA | Metabolite | LMST04010462 (LIPID MAPS) | |
7α-Hydroxy-3-oxochol- 4-en-24-oyl-glycine | Metabolite | LMST05030020 (LIPID MAPS) | |
7α-Hydroxy-3-oxochol- 4-en-24-oyl-taurine | Metabolite | LMST05040022 (LIPID MAPS) | |
7α-Hydroxy-3-oxocholest -4-en-(25R)26-oic acid | Metabolite | LMST04030242 (LIPID MAPS) | aka 7-Hydroxy-3-oxocholest-4-en-(25R)26-oic acid |
7α-Hydroxy-3-oxocholest -4-en-(25S)26-oyl-CoA | Metabolite | LMST04030253 (LIPID MAPS) | aka 7α-Hydroxy-3-oxocholest-4-en-(25S)26-oyl-CoA |
7α-Hydroxy-3-oxocholest- 4,24(E)-dien-26-oyl-CoA | Metabolite | LMST04030258 (LIPID MAPS) | |
7α-Hydroxycholesterol | Metabolite | LMST01010013 (LIPID MAPS) | AKA 7α-hydroxycholesterol (7α-HC) |
7α−Hydroxycholest -4-en-3-one | Metabolite | CHEBI:17899 (ChEBI) |
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7α−Hydroxycholest -4-en-3-one | Metabolite | LMST04030123 (LIPID MAPS) | aka 7α-hydroxycholest-4-en-3-one |
7β,(25R)26-Dihydroxycholesterol | Metabolite | LMST04030178 (LIPID MAPS) | AKA 7β,26-dihydroxycholesterol (7β,26-diHC). |
7β-Hydroxycholesterol | Metabolite | LMST01010047 (LIPID MAPS) | AKA 7β-hydroxycholesterol (7β-HC) |
ACOT11 | Protein | Q8WXI4 (Uniprot-TrEMBL) | |
ACOT12 | Protein | Q8WYK0 (Uniprot-TrEMBL) | |
ACOT13 | Protein | Q9NPJ3 (Uniprot-TrEMBL) | |
ACOT15 | Protein | Q8N1Q8 (Uniprot-TrEMBL) | |
ACOT1 | Protein | Q86TX2 (Uniprot-TrEMBL) | |
ACOT2 | Protein | P49753 (Uniprot-TrEMBL) | "originally thought to be in peroxisome [PMID:10944470)], later found to be mitochondrial [PMID:16940157]" [https://www.uniprot.org/uniprot/P49753] |
ACOT | Protein | 3.1.2.2 (Enzyme Nomenclature) | acyl-CoA thioesterase are a group of enzymes |
ACOT4 | Protein | Q8N9L9 (Uniprot-TrEMBL) | "Compared to mouse peroxisomal succinyl-coenzyme A thioesterase/ACOT4, the human enzyme has a broad substrate specificity overlapping the activity of three mouse acyl-coenzyme A thioesterases, providing an explanation for the unexpectedly low number of acyl-coenzyme A thioesterase genes in the human genome [PMID:16940157]" [https://www.uniprot.org/uniprot/Q8N9L9] |
ACOT6 | Protein | Q3I5F7 (Uniprot-TrEMBL) | |
ACOT7L | Protein | Q6ZUV0 (Uniprot-TrEMBL) | "Could be the product of a pseudogene. The peptide used to produce antibodies against ACOT7L matches at 85% with ACOT7 and the antibodies may not be specific to ACOT7L." [https://www.uniprot.org/uniprot/Q6ZUV0] |
ACOT7 | Protein | O00154 (Uniprot-TrEMBL) | |
ACOT8 | Protein | O14734 (Uniprot-TrEMBL) | |
ACOT9 | Protein | Q9Y305 (Uniprot-TrEMBL) | |
ACOX2 | GeneProduct | ACOX2 (HGNC) | |
AKR1C4 | GeneProduct | AKR1C4 (HGNC) | |
AKR1D1 | GeneProduct | AKR1D1 (HGNC) | |
AMACR | GeneProduct | AMACR (HGNC) |
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BA-delta5-3beta,7beta-diol 7betaGlcNAc | Metabolite | LMST04010467 (LIPID MAPS) | |
BAAT | GeneProduct | BAAT (HGNC) | amino acid N-acyl transferase |
BACS (SLC27A5) | GeneProduct | SLC27A5 (HGNC) |
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CH25H | Protein | O95992 (Uniprot-TrEMBL) | AKA cholesterol 25-hydroxylase |
CYP27A1 | GeneProduct | CYP27A1 (HGNC) | |
CYP27A1 | Protein | Q02318 (Uniprot-TrEMBL) | |
CYP39A1 | GeneProduct | CYP39A1 (HGNC) | Mostly expressed in liver, also in brain [PMID:24309898,25409824 (mouse)] |
CYP3A4 | GeneProduct | CYP3A4 (HGNC) | Alternative protein to CH25H for hydroxylation |
CYP3A4 | Protein | P08684 (Uniprot-TrEMBL) | Reaction also occurs in mouse: CYP3A11 |
CYP46A1 | Protein | Q9Y6A2 (Uniprot-TrEMBL) | Responsible for cholesterol homeostasis in brain [PMID:8790411]. Expressed mainly in Brain, however also small quantities in testis and ovary [PMID:24309898,25409824(mouse)]. |
CYP7A1 | Protein | P22680 (Uniprot-TrEMBL) |
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CYP7B1 | Protein | O75881 (Uniprot-TrEMBL) | |
CYP8B1 | GeneProduct | CYP8B1 (HGNC) | |
ChEH | Protein | P34913 (Uniprot-TrEMBL) |
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Chenodeoxycholic acid | Metabolite | LMST04010032 (LIPID MAPS) | |
Cholestane-3β, 5α,6β-triol | Metabolite | LMST01010510 (LIPID MAPS) |
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Cholesterol | Metabolite | LMST01010001 (LIPID MAPS) | |
Cholic acid | Metabolite | LMST04010001 (LIPID MAPS) | |
D8D7I | Protein | Q15125 (Uniprot-TrEMBL) |
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DBP | GeneProduct | DBP (HGNC) | D-biofinctional protein; aka MFE2, HSD17B4 |
DHCR7 | Protein | Q9UBM7 (Uniprot-TrEMBL) | |
Dendrogenin A | Metabolite | LMST05050025 (LIPID MAPS) | AKA Dendrogenin A |
EBI2 | Protein | P32249 (Uniprot-TrEMBL) | |
Estrogen receptor alpha | Protein | P03372 (Uniprot-TrEMBL) | Expressed in vascular cells. |
Estrogen receptor beta | Protein | Q92731 (Uniprot-TrEMBL) | Expressed in vascular cells. |
HSD11B1 | Protein | P28845 (Uniprot-TrEMBL) | |
HSD11B2 | Protein | P80365 (Uniprot-TrEMBL) | |
HSD3B7 | GeneProduct | HSD3B7 (HGNC) | |
HSD3B7 | Protein | Q9H2F3 (Uniprot-TrEMBL) | |
IL-17A | Protein | Q16552 (Uniprot-TrEMBL) | "IL-17 familiy is essential in host defense and may play key pathogenic roles in autoimmune diseases." [PMID: 25092323] |
IL-17B | Protein | Q9UHF5 (Uniprot-TrEMBL) | "IL-17 familiy is essential in host defense and may play key pathogenic roles in autoimmune diseases." [PMID: 25092323] |
IL-17C | Protein | Q9P0M4 (Uniprot-TrEMBL) | "IL-17 familiy is essential in host defense and may play key pathogenic roles in autoimmune diseases." [PMID: 25092323] |
IL-17D | Protein | Q8TAD2 (Uniprot-TrEMBL) | "IL-17 familiy is essential in host defense and may play key pathogenic roles in autoimmune diseases." [PMID: 25092323] |
IL-17E | Protein | Q9H293 (Uniprot-TrEMBL) | "IL-17 familiy is essential in host defense and may play key pathogenic roles in autoimmune diseases." [PMID: 25092323] |
IL-17F | Protein | Q96PD4 (Uniprot-TrEMBL) | "IL-17 familiy is essential in host defense and may play key pathogenic roles in autoimmune diseases." [PMID: 25092323] |
INSIG | Protein | O15503 (Uniprot-TrEMBL) | |
LBP | GeneProduct | LBP (HGNC) | L-bifunctional protein, aka MFP1, enoyl-CoA hydratase and 3-hydroxacyl CoA dehydrogenase EHHADH). |
LXR-alpha | Protein | P13133 (Uniprot-TrEMBL) | |
LXR-beta | Protein | P55055 (Uniprot-TrEMBL) | |
PXR | Protein | O75469 (Uniprot-TrEMBL) | |
ROR-γt | Protein | F1D8P6 (Uniprot-TrEMBL) |
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SCPx (SCP2) | GeneProduct | SCP2 (HGNC) | |
SULT2A1 | GeneProduct | Q06520 (Uniprot-TrEMBL) | |
SULT2B1 | GeneProduct | O00204 (Uniprot-TrEMBL) | |
UGT3A1 | GeneProduct | Q6NUS8 (Uniprot-TrEMBL) | |
VLCS (SLC27A2) | GeneProduct | SLC27A2 (HGNC) |
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histamine | Metabolite | Q61233 (Wikidata) |
Annotated Interactions
View all... |
Source | Target | Type | Database reference | Comment |
---|---|---|---|---|
25-Hydroxycholesterol | 7α,25-Dihydroxycholesterol | mim-conversion | 24309 (Rhea) | |
7α,25-Dihydroxycholesterol | 7α,25-Dihydroxycholest -4-en-3-one | mim-conversion | 47157 (Rhea) | |
7α-Hydroxycholesterol | 7α−Hydroxycholest -4-en-3-one | mim-conversion | 11897 (Rhea) | oxidation |
Cholesterol | (25R)26-Hydroxycholesterol | mim-conversion | 46401 (Rhea) | |
Cholesterol | 24S-hydroxycholesterol | mim-conversion | 22717 (Rhea) | |
Cholesterol | 25-Hydroxycholesterol | mim-conversion | 21105 (Rhea) | |
Cholesterol | 7α-Hydroxycholesterol | mim-conversion | 21813 (Rhea) | 7α-hydroxylation |