4-Cholesten-3-one

4-Cholesten-3-one is a lipid of Sterol Lipids (ST) class. 4-cholesten-3-one is associated with abnormalities such as Dehydration, Xanthomatosis, Cerebrotendinous, Peripheral Neuropathy, L.mexicana and Xanthoma. The involved functions are known as CYP27A1activity, 25-hydroxycholesterol 7alpha-hydroxylase activity, Biochemical Pathway, Anabolism and Oxidation. 4-cholesten-3-one often locates in Mitochondria, Liver, Body tissue, Hepatic, Mitochondria and Endothelium of artery. The associated genes with 4-Cholesten-3-one are P4HTM gene, tryptones and Regulon. The related lipids are Cholestenones, 7-hydroxy-4-cholesten-3-one, cholest-4-en-3-one, 25-hydroxycholesterol and 24-hydroxycholesterol.

Cross Reference

Introduction

To understand associated biological information of 4-Cholesten-3-one, we collected biological information of abnormalities, associated pathways, cellular/molecular locations, biological functions, related genes/proteins, lipids and common seen animal/experimental models with organized paragraphs from literatures.

What diseases are associated with 4-Cholesten-3-one?

4-Cholesten-3-one is suspected in Dehydration, Xanthomatosis, Cerebrotendinous, Peripheral Neuropathy, L.mexicana, Xanthoma, Rare Diseases and other diseases in descending order of the highest number of associated sentences.

Related references are mostly published in these journals:

Disease Cross reference Weighted score Related literature
Loading... please refresh the page if content is not showing up.

No disease MeSH terms mapped to the current reference collection.

PubChem Associated disorders and diseases

What pathways are associated with 4-Cholesten-3-one

Lipid pathways are not clear in current pathway databases. We organized associated pathways with 4-Cholesten-3-one through full-text articles, including metabolic pathways or pathways of biological mechanisms.

Related references are published most in these journals:

Pathway name Related literatures
Loading... please refresh the page if content is not showing up.

PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with 4-Cholesten-3-one?

Related references are published most in these journals:

Location Cross reference Weighted score Related literatures
Loading... please refresh the page if content is not showing up.

What functions are associated with 4-Cholesten-3-one?


Related references are published most in these journals:

Function Cross reference Weighted score Related literatures

What lipids are associated with 4-Cholesten-3-one?

Related references are published most in these journals:

Lipid concept Cross reference Weighted score Related literatures
Loading... please refresh the page if content is not showing up.

What genes are associated with 4-Cholesten-3-one?

Related references are published most in these journals:


Gene Cross reference Weighted score Related literatures

What common seen animal models are associated with 4-Cholesten-3-one?

There are no associated biomedical information in the current reference collection.

NCBI Entrez Crosslinks

All references with 4-Cholesten-3-one

Download all related citations
Per page 10 20 50 100 | Total 397
Authors Title Published Journal PubMed Link
Ooi LG and Liong MT Cholesterol-lowering effects of probiotics and prebiotics: a review of in vivo and in vitro findings. 2010 Int J Mol Sci pmid:20640165
Ismail SI and Mazen IA A study of gender outcome of Egyptian patients with 46,XY disorder of sex development. 2010 Sex Dev pmid:20664246
Martin LJ Olesoxime, a cholesterol-like neuroprotectant for the potential treatment of amyotrophic lateral sclerosis. 2010 IDrugs pmid:20721828
Wang X et al. Establishment of a novel model for studying the effects of extracts of Chinese herb medicine on human type II 5alpha-reductase in vitro. 2010 Yakugaku Zasshi pmid:20823678
Johnston JB et al. Functional redundancy of steroid C26-monooxygenase activity in Mycobacterium tuberculosis revealed by biochemical and genetic analyses. 2010 J. Biol. Chem. pmid:20843794
Driscoll MD et al. Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen. 2010 J. Biol. Chem. pmid:20889498
Edrees MM et al. Antimicrobial, antitumor and 5α-reductase inhibitor activities of some hydrazonoyl substituted pyrimidinones. 2010 Eur J Med Chem pmid:20933305
Roth MY et al. Steady-state pharmacokinetics of oral testosterone undecanoate with concomitant inhibition of 5α-reductase by finasteride. 2011 Int. J. Androl. pmid:20969601
Aloisi AM et al. Aromatase and 5-alpha reductase gene expression: modulation by pain and morphine treatment in male rats. 2010 Mol Pain pmid:20977699
Lin AS et al. Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp. 2010 Bioorg. Med. Chem. pmid:21036050
Dušková M and Pospíšilová H The role of non-aromatizable testosterone metabolite in metabolic pathways. 2011 Physiol Res pmid:21114370
DeBarber AE et al. Profiling sterols in cerebrotendinous xanthomatosis: utility of Girard derivatization and high resolution exact mass LC-ESI-MS(n) analysis. 2011 J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. pmid:21168372
Uhía I et al. Initial step in the catabolism of cholesterol by Mycobacterium smegmatis mc2 155. 2011 Environ. Microbiol. pmid:21208358
Martin LJ et al. The mitochondrial permeability transition pore regulates nitric oxide-mediated apoptosis of neurons induced by target deprivation. 2011 J. Neurosci. pmid:21209222
Finelli A et al. Impact of 5α-reductase inhibitors on men followed by active surveillance for prostate cancer. 2011 Eur. Urol. pmid:21211899
Ho CK and Habib FK Estrogen and androgen signaling in the pathogenesis of BPH. 2011 Nat Rev Urol pmid:21228820
Bortolato M et al. Isolation rearing-induced reduction of brain 5α-reductase expression: relevance to dopaminergic impairments. 2011 Neuropharmacology pmid:21256141
Wu YG et al. Testosterone, not 5α-dihydrotestosterone, stimulates LRH-1 leading to FSH-independent expression of Cyp19 and P450scc in granulosa cells. 2011 Mol. Endocrinol. pmid:21273442
Cha EK and Shariat SF The use of 5α-reductase inhibitors for the prevention and treatment of prostate cancer. 2011 Eur. Urol. pmid:21277077
Sato K et al. Increased muscular dehydroepiandrosterone levels are associated with improved hyperglycemia in obese rats. 2011 Am. J. Physiol. Endocrinol. Metab. pmid:21285401
Niu Y et al. Reduced levels of 5-α reductase 2 in adult prostate tissue and implications for BPH therapy. 2011 Prostate pmid:21308715
Kang HJ et al. The first successful paternity through in vitro fertilization-intracytoplasmic sperm injection with a man homozygous for the 5α-reductase-2 gene mutation. 2011 Fertil. Steril. pmid:21334614
Guardiola-Serrano F et al. Palmitoylation of human FasL modulates its cell death-inducing function. 2010 Cell Death Dis pmid:21368861
Jusakul A et al. Mechanisms of oxysterol-induced carcinogenesis. 2011 Lipids Health Dis pmid:21388551
Graupp M et al. Association of genetic variants in the two isoforms of 5α-reductase, SRD5A1 and SRD5A2, in lean patients with polycystic ovary syndrome. 2011 Eur. J. Obstet. Gynecol. Reprod. Biol. pmid:21530059
Askarova S et al. Impacts of membrane biophysics in Alzheimer's disease: from amyloid precursor protein processing to aβ Peptide-induced membrane changes. 2011 Int J Alzheimers Dis pmid:21547213
Nicholson TM and Ricke WA Androgens and estrogens in benign prostatic hyperplasia: past, present and future. 2011 Nov-Dec Differentiation pmid:21620560
Aggarwal S et al. QSAR studies on human 5alpha-reductase inhibitors: unsaturated 3-carboxysteroids. 2011 May-Jun Acta Pol Pharm pmid:21648201
Baudrand R et al. Overexpression of hepatic 5α-reductase and 11β-hydroxysteroid dehydrogenase type 1 in visceral adipose tissue is associated with hyperinsulinemia in morbidly obese patients. 2011 Metab. Clin. Exp. pmid:21704348
Mohler JL et al. Potential prostate cancer drug target: bioactivation of androstanediol by conversion to dihydrotestosterone. 2011 Clin. Cancer Res. pmid:21705451
Arellano Y et al. New ester derivatives of dehydroepiandrosterone as 5α-reductase inhibitors. 2011 Steroids pmid:21729714
Lei H et al. [Sterols of marine bryozoan Bugula neritina from the South China Sea]. 2011 Zhong Yao Cai pmid:21823470
de Almeida CL et al. Bioactivities from marine algae of the genus Gracilaria. 2011 Int J Mol Sci pmid:21845096
Chen L et al. [Active ingredients of Plastrum Testudinis inhibit epidermal stem cell apoptosis in serum-deprived culture]. 2011 Zhong Xi Yi Jie He Xue Bao pmid:21849150
Cai LQ et al. 17α-Estradiol and genistein inhibit high fat diet induced prostate gene expression and prostate growth in the rat. 2011 J. Urol. pmid:21855913
Le Lay S et al. Caveolin-1-mediated apolipoprotein A-I membrane binding sites are not required for cholesterol efflux. 2011 PLoS ONE pmid:21858084
Paris JJ et al. Inhibition of 5α-reductase activity in late pregnancy decreases gestational length and fecundity and impairs object memory and central progestogen milieu of juvenile rat offspring. 2011 J. Neuroendocrinol. pmid:21914008
Sen S et al. Restoration of IFNγR subunit assembly, IFNγ signaling and parasite clearance in Leishmania donovani infected macrophages: role of membrane cholesterol. 2011 PLoS Pathog. pmid:21931549
Griffin JE et al. High-resolution phenotypic profiling defines genes essential for mycobacterial growth and cholesterol catabolism. 2011 PLoS Pathog. pmid:21980284
Yarrow JF et al. Intracrine and myotrophic roles of 5α-reductase and androgens: a review. 2012 Med Sci Sports Exerc pmid:21988936
Marques MP et al. Continuous steroid biotransformations in microchannel reactors. 2012 N Biotechnol pmid:22008387
Jusakul A et al. Liver fluke-induced hepatic oxysterols stimulate DNA damage and apoptosis in cultured human cholangiocytes. 2012 Mutat. Res. pmid:22044627
Husain GM et al. Hypolipidemic and Antiobesity-Like Activity of Standardised Extract of Hypericum perforatum L. in Rats. 2011 ISRN Pharmacol pmid:22084716
Djavan B et al. Testosterone in prostate cancer: the Bethesda consensus. 2012 BJU Int. pmid:22129242
Joo SH et al. Biosynthesis of a cholesterol-derived brassinosteroid, 28-norcastasterone, in Arabidopsis thaliana. 2012 J. Exp. Bot. pmid:22170941
Li J et al. Androgen regulation of 5α-reductase isoenzymes in prostate cancer: implications for prostate cancer prevention. 2011 PLoS ONE pmid:22194926
Lange Y et al. Activation mobilizes the cholesterol in the late endosomes-lysosomes of Niemann Pick type C cells. 2012 PLoS ONE pmid:22276143
Mieczkowska J et al. Changes in the activity of connective tissue matrix enzymes in the metabolic syndrome. 2011 Arch Med Sci pmid:22291799
Magalon K et al. Olesoxime accelerates myelination and promotes repair in models of demyelination. 2012 Ann. Neurol. pmid:22367994
Chen DM et al. [The relationship of serum testosterone and its related index with the metabolism syndrome in women at perimenopausal or postmenopausal periods]. 2012 Zhonghua Fu Chan Ke Za Zhi pmid:22455743
Kasashima S et al. Expression of 5α-reductase in apocrine carcinoma of the breast and its correlation with clinicopathological aggressiveness. 2012 Histopathology pmid:22486281
Wollam J et al. A novel 3-hydroxysteroid dehydrogenase that regulates reproductive development and longevity. 2012 PLoS Biol. pmid:22505847
Kumar M et al. Cholesterol-lowering probiotics as potential biotherapeutics for metabolic diseases. 2012 Exp Diabetes Res pmid:22611376
Martel C et al. Inhibition of the Mitochondrial Permeability Transition for Cytoprotection: Direct versus Indirect Mechanisms. 2012 Biochem Res Int pmid:22675634
Muto A et al. Detection of Δ4-3-oxo-steroid 5β-reductase deficiency by LC-ESI-MS/MS measurement of urinary bile acids. 2012 J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. pmid:22695323
Biswas A et al. Influence of pioglitazone on experimental heart failure and hyperlipidemia in rats. 2012 Indian J Pharmacol pmid:22701242
Pan L et al. Sterols with antileishmanial activity isolated from the roots of Pentalinon andrieuxii. 2012 Phytochemistry pmid:22840389
Cieślak J et al. Convenient and efficient approach to the permanent or reversible conjugation of RNA and DNA sequences with functional groups. 2012 Curr Protoc Nucleic Acid Chem pmid:22956458
Gupta Y et al. Kinetic analysis of LDL oxidation in IHD and IHD risk subjects in Indian population. 2003 Indian J Clin Biochem pmid:23105369
García-Fernández E et al. A highly conserved mycobacterial cholesterol catabolic pathway. 2013 Environ. Microbiol. pmid:23489718
Benesch MG et al. A DSC and FTIR spectroscopic study of the effects of the epimeric 4-cholesten-3-ols and 4-cholesten-3-one on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes: comparison with their 5-cholesten analogues. 2014 Chem. Phys. Lipids pmid:24296232
Bouvaine S et al. A dietary test of putative deleterious sterols for the aphid Myzus persicae. 2014 PLoS ONE pmid:24465993
Neuvonen M et al. Enzymatic oxidation of cholesterol: properties and functional effects of cholestenone in cell membranes. 2014 PLoS ONE pmid:25157633
Walters JR et al. The response of patients with bile acid diarrhoea to the farnesoid X receptor agonist obeticholic acid. 2015 Aliment. Pharmacol. Ther. pmid:25329562
Lin CW et al. Substrate uptake and subcellular compartmentation of anoxic cholesterol catabolism in Sterolibacterium denitrificans. 2015 J. Biol. Chem. pmid:25418128
Chen M et al. The rate-determining steps of aldo-keto reductases (AKRs), a study on human steroid 5β-reductase (AKR1D1). 2015 Chem. Biol. Interact. pmid:25500266
Wijnberg JB and de Groot A Synthesis and 13C-NMR analysis of 5 alpha- and 5 beta-cholestane-3,6-dione. 1989 Steroids pmid:2588307
Chen L et al. A new ent-kaurane diterpenoid from Ixora amplexicaulis. 2016 Nat. Prod. Res. pmid:25941744
Sugano S et al. Sensitive assay of cytochrome P450scc activity by high-performance liquid chromatography. 1989 Anal. Biochem. pmid:2610350
Mouzaki M et al. Bile Acids and Dysbiosis in Non-Alcoholic Fatty Liver Disease. 2016 PLoS ONE pmid:27203081
Chen CL et al. Cholest-4-en-3-one attenuates TGF-β responsiveness by inducing TGF-β receptors degradation in Mv1Lu cells and colorectal adenocarcinoma cells. 2017 J. Recept. Signal Transduct. Res. pmid:27401208
Ma J et al. 4-cholesten-3-one suppresses lung adenocarcinoma metastasis by regulating translocation of HMGB1, HIF1α and Caveolin-1. 2016 Cell Death Dis pmid:27899819
Donato LJ et al. Description of analytical method and clinical utility of measuring serum 7-alpha-hydroxy-4-cholesten-3-one (7aC4) by mass spectrometry. 2018 Clin. Biochem. pmid:29051033
Ghosh S et al. Cholesterol-oxidase-magnetic nanobioconjugates for the production of 4-cholesten-3-one and 4-cholesten-3, 7-dione. 2018 Bioresour. Technol. pmid:29413944
Batta AK et al. Chromatographic separation of putative precursors of cholestanol. 1988 Jul-Aug Steroids pmid:3247666
Kaul HK et al. Genotoxicity of two fecal steroids in murine colonic epithelium assessed by the sister chromatid exchange technique. 1987 Mutagenesis pmid:3328036
Yoshimoto T et al. Polyethylene glycol derivative-modified cholesterol oxidase soluble and active in benzene. 1987 Biochem. Biophys. Res. Commun. pmid:3479986
Buchmann MS et al. Metabolism of the cholestanol precursor cholesta-4,6-dien-3-one in different tissues. 1987 Biochim. Biophys. Acta pmid:3676336
Suzuki K et al. Characterization of cytotoxic steroids in human faeces and their putative role in the etiology of human colonic cancer. 1986 Cancer Lett. pmid:3802059
Stokes NA and Hylemon PB Characterization of delta 4-3-ketosteroid-5 beta-reductase and 3 beta-hydroxysteroid dehydrogenase in cell extracts of Clostridium innocuum. 1985 Biochim. Biophys. Acta pmid:3861198
Murphy PR et al. Binding of oxygenated cholesterol metabolites to antiestrogen binding sites from chicken liver. 1985 Biochem. Biophys. Res. Commun. pmid:3985957
Schuster RE and Bennett RD A direct low temperature 1H and 19F nuclear magnetic resonance study of boron trifluoride complexes with 4-cholesten-3-one, 1(5beta)-androstene-3,17-dione, 5beta-androstane-3,17-dione, and obacunone. 1973 J. Org. Chem. pmid:4733449
Motlík K and Stárka L 4-Cholesten-3-one-induced lipoid hyperplasia of the adrenal cortex in rats. 1983 Acta Univ Carol Med (Praha) pmid:6637679
Nakagawa Y et al. Transfer of steroids and alpha-tocopherol between liposomal membranes. 1980 J. Biochem. pmid:6892636
Trinder P Oxidase determination of plasma cholesterol as cholest-4-en-3-one using iso-octane extraction. 1981 Ann. Clin. Biochem. pmid:6942786
Skrede S and Björkhem I Biosynthesis of cholestanol from intestinal 7 alpha-hydroxy-4-cholesten-3-one. 1982 J. Biol. Chem. pmid:7045120
Gallo LL et al. Enzymatic assay for cholesterol ester hydrolase activity. 1978 J. Lipid Res. pmid:712250
Aringer L 7-Hydroxylation of 3-oxygenated C27-, C28-, and C29-steroids in rat liver 18,000 g supernate. 1978 J. Lipid Res. pmid:731128
Slotte JP Direct observation of the action of cholesterol oxidase in monolayers. 1995 Biochim. Biophys. Acta pmid:7488639
Suzuki K Anti-obesity effect of cholest-4-en-3-one, an intestinal catabolite of cholesterol, on mice. 1993 J. Nutr. Sci. Vitaminol. pmid:8120678
Slotte JP and Ostman AL Oxidation/isomerization of 5-cholesten-3 beta-ol and 5-cholesten-3-one to 4-cholesten-3-one in pure sterol and mixed phospholipid-containing monolayers by cholesterol oxidase. 1993 Biochim. Biophys. Acta pmid:8431456
Molnár I et al. Bacterial cholesterol oxidases are able to act as flavoprotein-linked ketosteroid monooxygenases that catalyse the hydroxylation of cholesterol to 4-cholesten-6-ol-3-one. 1993 Mol. Microbiol. pmid:8459768
Plemenitas A et al. Identification of progesterone binding sites in the plasma membrane of the filamentous fungus Cochliobolus lunatus. 1993 J. Steroid Biochem. Mol. Biol. pmid:8499335
Bartram HP et al. Effects of fish oil on fecal bacterial enzymes and steroid excretion in healthy volunteers: implications for colon cancer prevention. 1996 Nutr Cancer pmid:8837863
Smith AG and Brooks CJ The mechanism of the isomerization of Cholest-5-en-3-one to cholest-4-en-3-one by cholesterol oxidase [proceedings]. 1977 Biochem. Soc. Trans. pmid:913789
Lin HS et al. Synthesis of 4 alpha-(2-propenyl)-5,6-secocholestan-3 alpha-ol, a novel B-ring seco analog of the hypocholesterolemic agent 4 alpha-(2-propenyl)-5 alpha-cholestan-3 alpha-ol. 1998 Steroids pmid:9589554
Suzuki K et al. The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice. 1998 Bioorg. Med. Chem. Lett. pmid:9873500