Compounds > 4,4-dimethylcholesta-8,14,24-trienol
Page last updated: 2024-11-08

4,4-dimethylcholesta-8,14,24-trienol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4,4-dimethylcholesta-8,14,24-trienol: a meiosis activating sterol; RN given refers to (5alpha,3beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID443212
CHEMBL ID10850
CHEBI ID17813
SCHEMBL ID2507968
MeSH IDM0263448

Synonyms (29)

Synonym
cholesta-8,14,24-trien-3-ol, 4,4-dimethyl-, (3beta,5alpha)-
(3beta,5alpha)-4,4-dimethylcholesta-8,14,24-trien-3-ol
CHEBI:17813 ,
4,4-dimethylcholesta-8(9),14,24-trien-3beta-ol
4,4-dimethylcholesta-8,14,24-trienol
4,4-dimechol-8,14,24-trienol
64284-64-6
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol
4,4-dimethylcholesta-8,11,24-trienol
4,4-dimethylcholesta-8,11,24-trien-3beta-ol
LMST01010149
CHEMBL10850
ff-mas
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3-ol
(3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2r)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol
4,4-dimethyl-5a-cholesta-8,14,24-trien-3b-ol
SCHEMBL2507968
4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol
17-(1,5-dimethylhex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7, 10,11,12,13,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol
4,4-dimethyl-cholesta-8,14,24-trienol
4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
(3beta,5alpha)-4,4-dimethyl-cholesta-8,14,24-trien-3-ol
4,4-dimethylcholesta-8,14,24-trien-3-olato
DTXSID20982834
Q27102638
(3r,5s,10s,13s,17s)-4,4,10,13-tetramethyl-17-[(2r)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol
(3beta,5alpha)-4,4-dimethylcholesta-8,14,24-trien-3-ol(contain up to 15per cent 25 isomer)
CS-0135564
HY-N7710

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The ovarian 4,4-dimethylsterol response was followed with regard to time and dose-response to the gonadotropins and the resumption of meiosis was evaluated using histologic sections."( Gonadotropin-induced accumulation of 4,4-dimethylsterols in mouse ovaries and its temporal relation to meiosis.
Baltsen, M, 2001)		0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metaboliteAny fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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]

Drug Classes (2)

ClassDescription
3beta-sterolA sterol in which the hydroxy group at position 3 has beta- configuration.
Delta(14) steroidAny steroid that contains a double bond between positions 14 and 15.
[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]

Pathways (49)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Metabolism of steroids111135
Cholesterol biosynthesis2249
Biological oxidations150276
Phase I - Functionalization of compounds69175
Cytochrome P450 - arranged by substrate type30110
Endogenous sterols1838
Steroid Biosynthesis2142
Smith-Lemli-Opitz Syndrome (SLOS)2142
CHILD Syndrome2142
Desmosterolosis2142
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)2142
Lysosomal Acid Lipase Deficiency (Wolman Disease)2142
Ibandronate Action Pathway2143
Simvastatin Action Pathway2143
Pravastatin Action Pathway2143
Rosuvastatin Action Pathway2143
Alendronate Action Pathway2143
Hypercholesterolemia2142
Lovastatin Action Pathway2143
Zoledronate Action Pathway2143
Cerivastatin Action Pathway2143
Risedronate Action Pathway2143
Pamidronate Action Pathway2143
Fluvastatin Action Pathway2143
Atorvastatin Action Pathway2143
Cholesteryl Ester Storage Disease2142
Hyper-IgD Syndrome2142
Mevalonic Aciduria2142
Wolman Disease2142
Cholesterol biosynthesis and metabolism CE(14:0)2250
Cholesterol biosynthesis and metabolism CE(10:0)2250
Cholesterol Biosynthesis and Metabolism CE(12:0)2250
Cholesterol Biosynthesis and Metabolism CE(16:0)2250
Cholesterol biosynthesis and metabolism CE(18:0)2250
Cholesterol metabolism with Bloch and Kandutsch-Russell pathways039
Cholesterol Biosynthesis and Metabolism2248
Bloch Pathway (Cholesterol Biosynthesis)929
cholesterol biosynthesis I428
zymosterol biosynthesis020
Cholesterol biosynthesis with skeletal dysplasias014
Cholesterol biosynthesis pathway in hepatocytes1137
Ergosterol biosynthesis332
superpathway of ergosterol biosynthesis I2156
zymosterol biosynthesis826
cholesterol biosynthesis I944
cholesterol biosynthesis III (via desmosterol)939
superpathway of cholesterol biosynthesis2178
superpathway of ergosterol biosynthesis2256
superpathway of sterol biosynthesis050

Bioassays (2)

Assay IDTitleYearJournalArticle
AID91834Compound was evaluated for meiosis inducing effect on immature mouse oocytes; Positive2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
Synthesis of FF-MAS from lithocholic acid.
AID140464Tested for ability to induce meiosis in immature mouse oocytes by measuring the rate of germinal vesicle breakdown (GVB)2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Meiosis activating sterols derived from diosgenin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (50)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (6.00)18.2507
2000's43 (86.00)29.6817
2010's3 (6.00)24.3611
2020's1 (2.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.82 (24.57)
Research Supply Index4.04 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (9.80%)5.53%
Reviews6 (11.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other40 (78.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
cilostamide
cilostamide: selective inhibitor of cyclic AMP phosphodiesterase & platelet aggregation; structure		2.0210quinolines
1-methyl-3-isobutylxanthine
1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.		2103-isobutyl-1-methylxanthine
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		2.4620dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source		2.0210chromones;
morpholines;
organochlorine compound		autophagy inhibitor;
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor;
geroprotector
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		2.0210monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		3.5120antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
17-alpha-hydroxyprogesterone
17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.		2.462017alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
tertiary alpha-hydroxy ketone		human metabolite;
metabolite;
mouse metabolite;
progestin
trans-1,4-bis(2-chlorobenzaminomethyl)cyclohexane dihydrochloride
trans-1,4-Bis(2-chlorobenzaminomethyl)cyclohexane Dihydrochloride: An anti-cholesteremic agent that inhibits delta 7-reductase, delta 14 reductase, and sterol biosynthesis.		3.1550
cyclic cmp
Cyclic CMP: A cyclic nucleotide formed from CYTIDINE TRIPHOSPHATE by the action of cytidylate cyclase. It is a potential cyclic nucleotide intracellular mediator of signal transductions.. 3',5'-cyclic CMP : A 3',5'-cyclic pyrimidine nucleotide having cytosine as the nucleobase.		2.02103',5'-cyclic pyrimidine nucleotidehuman metabolite
azalanstat
azalanstat: inhibits lanosterol 14 alpha-demethylase, the enzyme which catalyzes the first step in conversion of lanosterol to cholesterol in mammals; structure given in first source		2.0310
dibutyryl cyclic-3',5'-cytidine monophosphate
[no description available]		2.0210
4,4-dimethylcholesta-8,14-dien-3-ol
4,4-dimethylcholesta-8,14-dien-3-ol: RN refers to (3beta,5alpha)-isomer; a meiosis-activating sterol. 4,4-dimethyl-8,14-cholestadien-3beta-ol : A cholestanoid that is 5alpha-cholesta-8,14-dien-3beta-ol bearing two additional methyl substituents at position 4.		3.26603beta-sterol;
cholestanoid;
tetracyclic triterpenoid
lanosterol
[no description available]		4.729014alpha-methyl steroid;
3beta-sterol;
tetracyclic triterpenoid		bacterial metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
mevalonic acid
Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.		2103,5-dihydroxy-3-methylpentanoic acid
ergosterol
[no description available]		2.01103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite
dactinomycin
Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)		210actinomycinmutagen
amanitins
Amanitins: Cyclic peptides extracted from carpophores of various mushroom species. They are potent inhibitors of RNA polymerases in most eukaryotic species, blocking the production of mRNA and protein synthesis. These peptides are important in the study of transcription. Alpha-amanitin is the main toxin from the species Amanitia phalloides, poisonous if ingested by humans or animals.		210
menotropins
Menotropins: Extracts of urine from menopausal women that contain high concentrations of pituitary gonadotropins, FOLLICLE STIMULATING HORMONE and LUTEINIZING HORMONE. Menotropins are used to treat infertility. The FSH:LH ratio and degree of purity vary in different preparations.		210
bucladesine
Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.		2.7303',5'-cyclic purine nucleotide
epidermal growth factor
Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.		2.4220
hypoxanthine
[no description available]		3.5280nucleobase analogue;
oxopurine;
purine nucleobase		fundamental metabolite
zaprinast
zaprinast: anaphylaxis inhibitor; structure		210triazolopyrimidines
ConditionIndicatedRelationship StrengthStudiesTrials
Abnormalities, Congenital
[description not available]		02.9810
Abnormalities, Autosome
[description not available]		05.0233
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.4320
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)		02.0210
Adverse Drug Event
[description not available]		03.4111
Autosomal Chromosome Disorders
[description not available]		03.4111
Drug-Related Side Effects and Adverse Reactions
Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.		03.4111
Polycystic Ovarian Syndrome
[description not available]		02.7130
Polycystic Ovary Syndrome
A complex disorder characterized by infertility, HIRSUTISM; OBESITY; and various menstrual disturbances such as OLIGOMENORRHEA; AMENORRHEA; ANOVULATION. Polycystic ovary syndrome is usually associated with bilateral enlarged ovaries studded with atretic follicles, not with cysts. The term, polycystic ovary, is misleading.		02.7130
Polyploid
[description not available]		02.0310
Aneuploid
[description not available]		03.4211