ergosta-4,6,8(14),22-tetraen-3-one profile

ergosta-4,6,8(14),22-tetraen-3-one: antineoplastic, non-toxic fungal steroid [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ergosta-4,6,8(14),22-tetraen-3-one : An ergostanoid that is (22E)-ergosta-4,6,8(14),22-tetraene substituted by an oxo group at position 3. It has been isolated from the mycelia of Cordyceps sinensis. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	6441416
CHEMBL ID	3588948
CHEBI ID	69431
SCHEMBL ID	6365010
MeSH ID	M0065468

Synonym
(9r,10r,13r,17r)-17-[(e,2r,5r)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,9,11,12,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
ergosta-4,6,8(14),22-tetraen-3-one
unii-ri51y55u8p
19254-69-4
ri51y55u8p ,
ergosta-4,6,8(14),22-tetraen-3-one, (22e)-
(22e)-ergosta-4,6,8(14),22-tetraen-3-one
CHEBI:69431
24-methylcholesta-4,6,8(14),22-tetraen-3-one
ergone
(22e)-4,6,8(14),22-ergostatetraen-3-one
(22e,24r)-ergosta-4,6,8(14),22-tetraen-3-one
SCHEMBL6365010
AKOS022184779
CHEMBL3588948
Q27104972
nsc-785136
nsc785136
DTXSID201296846
FS-10533

Excerpt	Reference	Relevance
" In addition, ergone also possesses a strong cytotoxic effect against HepG-2 cells showing low toxic level for CC-1 cells."	( Cytotoxic effects of ergone, a compound isolated from Fulviformes fastuosus. Adhikari, A; de Silva, ED; Fernando, D; Nanayakkara, C; Soysa, P; Wijesundera, R, 2016)	0.43

Excerpt	Reference	Relevance
" The developed method has been successfully applied to the pharmacokinetic study of the drug in SD rats."	( A fast and sensitive HPLC-MS/MS analysis and preliminary pharmacokinetic characterization of ergone in rats. Chao, X; Cheng, XL; Lin, RC; Sun, WJ; Zhang, Y; Zhao, Y; Zhao, YY, 2010)	0.36
" Metabolism and pharmacokinetic studies on rat were conducted for ergone."	( Rapid resolution liquid chromatography-mass spectrometry and high-performance liquid chromatography-fluorescence detection for metabolism and pharmacokinetic studies of ergosta-4,6,8(14),22-tetraen-3-one. Cheng, XL; Li, XY; Lin, RC; Liu, XY; Qin, XY; Sun, WJ; Sun, XL; Zhang, Y; Zhao, YY, 2010)	0.56
" The method described herein had been successfully applied for the pharmacokinetic studies in male SD rats after administration of 20 mg/kg dose of solution of ergone."	( Quantitative HPLC method and pharmacokinetic studies of ergosta-4,6,8(14),22-tetraen-3-one, a natural product with diuretic activity from Polyporus umbellatus. Li, XY; Lin, RC; Qin, XY; Sun, WJ; Zhang, Y; Zhao, YY, 2010)	0.61

Excerpt	Relevance	Reference
" Since PEG liposome was able to stably encapsulate ergone in blood, area under plasma concentration-time curve of ergone was also extensively enhanced after intravenous dosing of ergone-PEG liposome into normal rats."	( Enhanced distribution and anti-tumor activity of ergosta-4,6,8(14),22-tetraen-3-one by polyethylene glycol liposomalization. Fan, J; Hu, X; Ji, Z; Liang, X; Sun, Y; Zhao, Y, 2013)	0.64

Role	Description
fungal metabolite	Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
ergostanoid
3-oxo-Delta(4) steroid	A 3-oxo steroid conjugated to a C=C double bond at the alpha,beta position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Assay ID	Title	Year	Journal	Article
AID1776944	Cytotoxicity against African green monkey MARC145 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay	2021	Journal of natural products, 06-25, Volume: 84, Issue:6	Sesquiterpenes and Steroids from an Endophytic
AID1233172	Antimicrobial activity against Staphylococcus aureus after 5 to 12 hrs by micro broth dilution assay	2015	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13	Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs.
AID1776947	Antiproliferative activity against human MDA-MB-231 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay	2021	Journal of natural products, 06-25, Volume: 84, Issue:6	Sesquiterpenes and Steroids from an Endophytic
AID1776946	Antiproliferative activity against human HeLa cells assessed as cell growth inhibition measured after 48 hrs by MTT assay	2021	Journal of natural products, 06-25, Volume: 84, Issue:6	Sesquiterpenes and Steroids from an Endophytic
AID1776948	Antibacterial activity against Staphylococcus aureus CMCC26003 assessed as bacterial growth inhibition by microbroth dilution method	2021	Journal of natural products, 06-25, Volume: 84, Issue:6	Sesquiterpenes and Steroids from an Endophytic
AID1233173	Antimicrobial activity against Escherichia coli after 5 to 12 hrs by micro broth dilution assay	2015	Bioorganic & medicinal chemistry letters, Jul-01, Volume: 25, Issue:13	Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs.
AID1776945	Antiproliferative activity against human MCF7 cells assessed as cell growth inhibition measured after 48 hrs by MTT assay	2021	Journal of natural products, 06-25, Volume: 84, Issue:6	Sesquiterpenes and Steroids from an Endophytic
AID1776949	Antibacterial activity against methicillin-resistant Staphylococcus aureus JCSC3063 assessed as bacterial growth inhibition by microbroth dilution method	2021	Journal of natural products, 06-25, Volume: 84, Issue:6	Sesquiterpenes and Steroids from an Endophytic
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (3.03)	18.7374
1990's	0 (0.00)	18.2507
2000's	8 (24.24)	29.6817
2010's	21 (63.64)	24.3611
2020's	3 (9.09)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.86%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	34 (97.14%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
adenine [no description available]	2.48	2	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.06	1	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.07	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.07	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
mannitol [no description available]	2.44	2	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.02	1
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	7.08	1	f-block element atom; lanthanoid atom
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.05	1	isocoumarins
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	2.31	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.11	1
ergosterol [no description available]	3.87	11	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.11	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
glycosides [no description available]	2.11	1
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.31	1	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
sesquiterpenes [no description available]	2.15	1
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2.11	1	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
tocopherylquinone tocopherylquinone: RN refers to (3R-(3R,7R,11R*))-isomer; structure	2.11	1
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	2.05	1	sphing-4-enine	human metabolite; mouse metabolite
trans-phytol trans-phytol: structure in first source	2.11	1	diterpenoid; long-chain primary fatty alcohol	algal metabolite; plant metabolite; schistosomicide drug
3,4-di-o-caffeoylquinic acid 3,4-di-O-caffeoylquinic acid: isolated from Siphonostegia chinensis	2.11	1	quinic acid
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	2.11	1	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	2.07	1	1-O-acyl-sn-glycero-3-phosphocholine
ergosterol-5,8-peroxide ergosterol-5,8-peroxide: also inhibits sulfatase; isolated from fungus Cercospora kikuchii; structure given in first source. ergosterol peroxide : An ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3beta,5alpha,8alpha,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities.	2.05	1	3beta-sterol; ergostanoid; organic peroxide; phytosterols	antimycobacterial drug; antineoplastic agent; metabolite; trypanocidal drug
methyl ferulate methyl ferulate: inhibits LDL oxidation; isolated from Chrysanthemum coronarium; structure in first source. trans-methylferulate : A cinnamate ester that is the methyl ester of ferulic acid. It has been isolated from Pisonia aculeata.	2.11	1	cinnamate ester; guaiacols; methyl ester	plant metabolite
4,5-di-O-caffeoylquinic acid [no description available]	2.11	1	quinic acid
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.11	1
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.05	1

Condition	Relationship Strength	Studies
Glial Cell Tumors [description not available]	2.11	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.11	1
Chronic Kidney Diseases [description not available]	2.1	1
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.1	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.13	1
Hepatocellular Carcinoma [description not available]	7.49	2
Experimental Hepatoma [description not available]	2.13	1
Cancer of Muscle [description not available]	2.13	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.49	2
Rhabdomyosarcoma A malignant solid tumor arising from mesenchymal tissues which normally differentiate to form striated muscle. It can occur in a wide variety of sites. It is divided into four distinct types: pleomorphic, predominantly in male adults; alveolar (RHABDOMYOSARCOMA, ALVEOLAR), mainly in adolescents and young adults; embryonal (RHABDOMYOSARCOMA, EMBRYONAL), predominantly in infants and children; and botryoidal, also in young children. It is one of the most frequently occurring soft tissue sarcomas and the most common in children under 15. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p2186; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, pp1647-9)	2.13	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.98	4
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.06	1
Acute Kidney Failure [description not available]	2.06	1
Cirrhosis [description not available]	2.06	1
Interstitial Nephritis [description not available]	2.06	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.06	1
Nephritis, Interstitial Inflammation of the interstitial tissue of the kidney. This term is generally used for primary inflammation of KIDNEY TUBULES and/or surrounding interstitium. For primary inflammation of glomerular interstitium, see GLOMERULONEPHRITIS. Infiltration of the inflammatory cells into the interstitial compartment results in EDEMA, increased spaces between the tubules, and tubular renal dysfunction.	2.06	1
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.06	1
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.06	1
Chronic Kidney Failure [description not available]	2.48	2
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	2.48	2
Bovine Diseases [description not available]	1.95	1
Plant Poisoning Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.	1.95	1
Symptom Cluster [description not available]	1.95	1
Syndrome A characteristic symptom complex.	1.95	1

ergosta-4,6,8(14),22-tetraen-3-one

Description

Cross-References

Synonyms (20)

Research Excerpts

Toxicity

Pharmacokinetics

Dosage Studied

Roles (1)

Drug Classes (2)

Bioassays (8)

Research

Studies (33)

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Research Demand Index: 10.92

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