Classification Term: 169965

Oxysterols (ontology term: bde9661ceabffe2b1f5e1c93c67cf6f2)

found 44 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Sterols

Child Taxonomies: There is no child term of current ontology term.

Wortmannin

11-(acetyloxy)-1S,6bR,7,8,9aS,10,11R,11bR-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione

C23H24O8 (428.1471)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D007329 - Insulin Antagonists C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C2152 - Phosphatidylinositide 3-Kinase Inhibitor D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D000890 - Anti-Infective Agents > D000935 - Antifungal Agents C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor D011838 - Radiation-Sensitizing Agents

   

25-Hydroxycholesterol

(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

C27H46O2 (402.3498)


25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498 ). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge. [HMDB] 25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 25-Hydroxycholesterol is a metabolite of cholesterol that is produced and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-hydroxycholesterol is a potent (EC50≈65 nM) and selective suppressor of IgA production by B cells.

   

5alpha-Cholestanone

(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

C27H46O (386.3548)


5alpha-Cholestanone, also known as 5α-cholestanone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanone is considered to be a sterol lipid molecule. 5alpha-Cholestanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is an oxidation product of coprosterol. It is a substrate of cholestenone 5alpha-reductase [EC 1.3.1.22] (KEGG). [HMDB] 5α-Cholestan-3-one is an endogenous metabolite.

   

Finasteride

(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide

C23H36N2O2 (372.2777)


Finasteride is only found in individuals that have used or taken this drug. Finasteride is an androgen antagonist. It is an orally active testosterone 5-alpha-reductase inhibitor. Finasteride is one of the currently available pharmacologic treatment modalities with proven efficacy for treatment of androgenetic alopecia. The mechanism of action has not been fully determined, but finasteride has shown to decrease scalp DHT concentration to the levels found in hairy scalp, reduce serum DHT, increase hair regrowth, and slow hair loss. Androgenetic alopecia (AGA), or male pattern hair loss, affects approximately 50\\% of the male population. AGA is an androgen-related condition in genetically predisposed individuals. There is no treatment to completely reverse AGA in advanced stages, but with medical treatment (e.g. finasteride), the progression can be arrested and partly reversed in the majority of patients who have mild to moderate AGA. Finasteride is also used as a surgical alternative for treatment of benign prostatic hyperplasia (PubChem). The mechanism of action of finasteride is based on its preferential inhibition of type II 5alpha-reductase through the formation of a stable complex with the enzyme. Inhibition of type II 5alpha-reductase blocks the peripheral conversion of testosterone to DHT (resulting in significant decreases in serum and tissue DHT concentrations), minimal to moderate increase in serum testosterone concentrations, and substantial increases in prostatic testosterone concentrations. As DHT appears to be the principal androgen responsible for stimulation of prostatic growth, a decrease in DHT concentrations will result in a decrease in prostatic volume (approximately 20-30\\% after 6-24 months of continued therapy). Finasteride may increase the sensitivity of prostate specific antigen to detect prostate cancer. At present, finasteride remains the only intervention shown in long-term prospective phase III clinical trials to reduce the incidence of prostate cancer (PMID: 18044109, 17543725, 17414641, 17415094, 17394699). Finasteride is an androgen antagonist. Finasteride is one of the currently available pharmacologic treatment modalities with proven efficacy for treatment of androgenetic alopecia. Androgenetic alopecia (AGA), or male pattern hair loss, affects approximately 50\\% of the male population. AGA is an androgen-related condition in genetically predisposed individuals. There is no treatment to completely reverse AGA in advanced stages, but with medical treatment (e.g., finasteride), the progression can be arrested and partly reversed in the majority of patients who have mild to moderate AGA. Finasteride may increase the sensitivity of prostate specific antigen to detect prostate cancer. At present, finasteride remains the only intervention shown in long-term prospective phase III clinical trials to reduce the incidence of prostate cancer. (PMID: 18044109, 17543725, 17414641, 17415094, 17394699) [HMDB] G - Genito urinary system and sex hormones > G04 - Urologicals > G04C - Drugs used in benign prostatic hypertrophy > G04CB - Testosterone-5-alpha reductase inhibitors D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D065088 - Steroid Synthesis Inhibitors D004791 - Enzyme Inhibitors > D065088 - Steroid Synthesis Inhibitors > D058891 - 5-alpha Reductase Inhibitors C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen D000089162 - Genitourinary Agents > D064804 - Urological Agents C471 - Enzyme Inhibitor > C2319 - 5 Alpha-Reductase Inhibitor C1892 - Chemopreventive Agent D - Dermatologicals

   

7beta-Hydroxycholesterol

(1S,2R,5S,9R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

C27H46O2 (402.3498)


7beta-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7beta-hydroxycholesterol is considered to be a sterol lipid molecule. 7beta-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7beta-Hydroxycholesterol has been identified in atheromatous plaques and in plasma of atherosclerotic patients (PMID: 16604541). 7beta-Hydroxycholesterol induces apoptosis in Caco-2 cells and alters lysosomal membrane integrity. It exhibits a specific enhancement of oxidative stress and of endonuclease G expression (PMID: 17136497). 7b-Hydroxycholesterol is identified in atheromatous plaques and in plasma of atherosclerotic patients.(PMID: 16604541)

   

5beta-Cholestanone

(1S,2S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

C27H46O (386.3548)


5beta-Cholestanone is an oxidation product of coprosterol. It is a substrate of cholestenone 5beta-reductase [EC 1.3.1.3] (KEGG). 5beta-cholestanone belongs to the family of Cholesterols and Derivatives. These are compounds containing an hydroxylated chloestane moeity.

   

24,25-Epoxycholesterol

14-[4-(3,3-dimethyloxiran-2-yl)butan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

C27H44O2 (400.3341)


   

wortmannin

18-(Methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]nonadeca-2(10),12(19),14-trien-3-yl acetic acid

C23H24O8 (428.1471)


   

22-Hydroxycholesterol

22-alpha-Hydroxy Cholesterol

C27H46O2 (402.3498)


   

Finasteride

(1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide

C23H36N2O2 (372.2777)


G - Genito urinary system and sex hormones > G04 - Urologicals > G04C - Drugs used in benign prostatic hypertrophy > G04CB - Testosterone-5-alpha reductase inhibitors D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D065088 - Steroid Synthesis Inhibitors D004791 - Enzyme Inhibitors > D065088 - Steroid Synthesis Inhibitors > D058891 - 5-alpha Reductase Inhibitors C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen D000089162 - Genitourinary Agents > D064804 - Urological Agents C471 - Enzyme Inhibitor > C2319 - 5 Alpha-Reductase Inhibitor C1892 - Chemopreventive Agent D - Dermatologicals CONFIDENCE standard compound; INTERNAL_ID 541; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9164; ORIGINAL_PRECURSOR_SCAN_NO 9159 CONFIDENCE standard compound; INTERNAL_ID 541; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9203; ORIGINAL_PRECURSOR_SCAN_NO 9201 CONFIDENCE standard compound; INTERNAL_ID 541; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9222; ORIGINAL_PRECURSOR_SCAN_NO 9221 CONFIDENCE standard compound; INTERNAL_ID 541; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9254; ORIGINAL_PRECURSOR_SCAN_NO 9252 CONFIDENCE standard compound; INTERNAL_ID 541; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9266; ORIGINAL_PRECURSOR_SCAN_NO 9265 CONFIDENCE standard compound; INTERNAL_ID 541; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9274; ORIGINAL_PRECURSOR_SCAN_NO 9273 CONFIDENCE standard compound; INTERNAL_ID 2702 CONFIDENCE standard compound; INTERNAL_ID 4115

   

1,25-Dihydroxycholesterol

cholest-5-ene-1alpha,3beta,25-triol

C27H46O3 (418.3447)


   

32-hydroxylanosterol

lanosta-8,24-dien-3beta,30-diol

C30H50O2 (442.3811)


   

24S,25-dihydroxycholesterol

cholest-5-en-3beta,24S,25-triol

C27H46O3 (418.3447)


   

24S,27-dihydroxycholesterol

cholest-5-en-3beta,24S,26-triol

C27H46O3 (418.3447)


   

25,27-dihydroxycholesterol

cholest-5-en-3beta,25,26-triol

C27H46O3 (418.3447)


   

6,24S-dihydroxycholesterol

cholest-5-en-3beta,6,24S-triol

C27H46O3 (418.3447)


   

24-oxocholesterol

24-oxo-cholest-5-en-3beta-ol

C27H44O2 (400.3341)


   

20S-hydroxycholesterol

cholest-5-en-3beta,20S-diol

C27H46O2 (402.3498)


   

CHOLESTANONE

CHOLESTANONE

C27H46O (386.3548)


   

Secosterol-A

Secosterol-A

C27H46O3 (418.3447)


   

Dihydroxycholesterol

Dihydroxycholesterol

C27H46O3 (418.3447)


   

22R-hydroxycholesterol

22-alpha-Hydroxy Cholesterol

C27H46O2 (402.3498)


An oxysterol that is the 22R-hydroxy derivative of cholesterol.

   

7alpha-Hydroxy-5beta-cholestan-3-one

7alpha-Hydroxy-5beta-cholestan-3-one

C27H46O2 (402.3498)


A 3-oxo-5beta-steroid that is 5beta-cholestan-3-one bearing an additional hydroxy substituent at position 7alpha .

   

25-Hydroxycholesterol

Cholest-5-ene-3beta,25-diol

C27H46O2 (402.3498)


25-Hydroxycholesterol is a metabolite of cholesterol that is produced and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-hydroxycholesterol is a potent (EC50≈65 nM) and selective suppressor of IgA production by B cells.

   

19-HYDROXYCHOLESTEROL

19-HYDROXYCHOLESTEROL

C27H46O2 (402.3498)


   

6alpha-hydroxycholestanol

6alpha-hydroxycholestanol

C27H48O2 (404.3654)


A sterol that is cholestanol in which the hydrogen at the 6alpha position has been replaced by a hydroxy group.

   

3-Oxo-7alpha-hydroxycholesterol

3-Oxo-7alpha-hydroxycholesterol

C27H44O2 (400.3341)


   

15alpha-Hydroxycholestane

15alpha-Hydroxycholestane

C27H48O2 (404.3654)


   

24R-Hydoxycholesterol

24R-Hydoxycholesterol

C27H46O2 (402.3498)


   

27-Hydroxycholesterol(25R)

(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,6R)-7-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

C27H46O2 (402.3498)


   

Epoxycholesterol

Epoxycholesterol

C27H44O2 (400.3341)


   

Hydoxycholesterol

Hydoxycholesterol

C27H46O2 (402.3498)


   

Hydroxycholestane

Hydroxycholestane

C27H48O2 (404.3654)


   

Hydroxycholestanol

Hydroxycholestanol

C27H48O2 (404.3654)


   

Hydroxycholestanone

Hydroxycholestanone

C27H46O2 (402.3498)


   

Hydroxycholesterol

Hydroxycholesterol

C27H46O2 (402.3498)


   

Hydroxylanosterol

Hydroxylanosterol

C30H50O2 (442.3811)


   

Ketocholestane

Ketocholestane

C27H46O2 (402.3498)


   

Ketocholestene

Ketocholestene

C27H44O2 (400.3341)


   

Norcholestanepentol

Norcholestanepentol

C26H46O5 (438.3345)


   

Oxocholestanol

Oxocholestanol

C27H46O2 (402.3498)


   

Oxocholesterol

Oxocholesterol

C27H44O2 (400.3341)


   

Oxohydroxycholesterol

Oxohydroxycholesterol

C27H44O2 (400.3341)


   

Oxolanosterol

Oxolanosterol

C30H48O2 (440.3654)