Compounds > 3alpha-hydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid
Page last updated: 2024-11-13

3alpha-hydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid

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

Description

zhankuic acid B: isolated from Antrodia cinnamomea; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

zhankuic acid B : A steroid acid that is ergosta-8,24(28)-dien-26-oic acid substituted by a hydroxy group at position 3, a methyl group at position 4 and oxo groups at positions 7 and 11 (the 3alpha,4alpha,5alpha stereoisomer). Isolated from Antrodia cinnamomea and Antrodia camphorata, it exhibits cytotoxic, anticholinergic and antiserotonergic activities. [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]

Cross-References

ID SourceID
PubMed CID53323940
CHEMBL ID1644790
CHEBI ID66504
SCHEMBL ID11885909
MeSH IDM0258416

Synonyms (8)

Synonym
bdbm50334066
CHEMBL1644790 ,
chebi:66504 ,
zhankuic acid b
(3alpha,4alpha,5alpha)-3-hydroxy-4-methyl-7,11-dioxoergosta-8,24(28)-dien-26-oic acid
3alpha-hydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid
SCHEMBL11885909
Q27135109
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
cholinergic antagonistAny drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
serotonergic antagonistDrugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
[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 (5)

ClassDescription
11-oxo steroidAny oxo steroid that has an oxo substituent at position 11.
7-oxo steroidAny oxo steroid carrying an oxo group at position 7.
3alpha-hydroxy steroidA 3-hydroxy steroid in which the 3-hydroxy substituent is in the alpha-position.
steroid acidAny steroid substituted by at least one carboxy group.
monocarboxylic acidAn oxoacid containing a single carboxy group.
[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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)9.60000.00103.39119.6000AID552870
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID550014Cytotoxicity against human KBVIN cells after 3 days by sulforhodamine B assay2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Camphoratins A-J, potent cytotoxic and anti-inflammatory triterpenoids from the fruiting body of Taiwanofungus camphoratus.
AID552866Cytotoxicity against human MCF7 cells after 3 days by MTT assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID552868Inhibition of mouse NOX activity in NADPH-induced mouse BV2 microglial cells assessed as NO production2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID552867Cytotoxicity against human HeLa cells after 3 days by MTT assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID552865Cytotoxicity against human Hep2 cells after 3 days by MTT assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID550017Antiinflammatory activity in human PMNC cells assessed as inhibition of fMLP-induced NOX-dependent ROS production up to 50 uM2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Camphoratins A-J, potent cytotoxic and anti-inflammatory triterpenoids from the fruiting body of Taiwanofungus camphoratus.
AID1247994Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced TNF-alpha production at 50 ug/ml2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Immunosuppressive effect of zhankuic acid C from Taiwanofungus camphoratus on dendritic cell activation and the contact hypersensitivity response.
AID1247995Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced IL-6 production at 50 ug/ml2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Immunosuppressive effect of zhankuic acid C from Taiwanofungus camphoratus on dendritic cell activation and the contact hypersensitivity response.
AID550016Antiinflammatory activity in mouse BV2 cells assessed as inhibition of NOX-dependent ROS production up to 50 uM2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Camphoratins A-J, potent cytotoxic and anti-inflammatory triterpenoids from the fruiting body of Taiwanofungus camphoratus.
AID552870Inhibition of iNOS in mouse BV2 microglial cells assessed as NO production2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID360214Cytotoxicity against mouse P388 cells after 72 hrs1995Journal of natural products, Nov, Volume: 58, Issue:11
New steroid acids from Antrodia cinnamomea, a fungal parasite of Cinnamomum micranthum.
AID550013Cytotoxicity against human KB cells after 3 days by sulforhodamine B assay2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Camphoratins A-J, potent cytotoxic and anti-inflammatory triterpenoids from the fruiting body of Taiwanofungus camphoratus.
AID1247996Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced IL-12 production at 50 ug/ml2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Immunosuppressive effect of zhankuic acid C from Taiwanofungus camphoratus on dendritic cell activation and the contact hypersensitivity response.
AID552869Inhibition of NOX in fMLP-induced PMN cells assessed as NO production2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID550015Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced iNOS-dependent nitrite production after 24 hrs by Griess method2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Camphoratins A-J, potent cytotoxic and anti-inflammatory triterpenoids from the fruiting body of Taiwanofungus camphoratus.
AID1247997Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced RANTES production at 50 ug/ml2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
Immunosuppressive effect of zhankuic acid C from Taiwanofungus camphoratus on dendritic cell activation and the contact hypersensitivity response.
AID552864Cytotoxicity against human DaOY cells after 3 days by MTT assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.87

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 Index12.87 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
diphenyleneiodonium
diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.		2.4620organic cation
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.0610mitomycinalkylating agent;
antineoplastic agent
etoposide
[no description available]		2.0510beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
ng-nitroarginine methyl ester
NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.		2.4620alpha-amino acid ester;
L-arginine derivative;
methyl ester;
N-nitro compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor
sesamin
(+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.		2.0610benzodioxoles;
furofuran;
lignan		antineoplastic agent;
neuroprotective agent;
plant metabolite
ergosterol
[no description available]		2.94403beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite
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.		2.46203beta-sterol;
ergostanoid;
organic peroxide;
phytosterols		antimycobacterial drug;
antineoplastic agent;
metabolite;
trypanocidal drug
4alpha-methylergosta-8,24(28)-dien-3,7,11-trione-26-oic acid
zhankuic acid A: isolated from Antrodia cinnamomea; structure in first source. zhankuic acid A : A steroid acid that is ergosta-8,24(28)-dien-26-oic acid substituted by a methyl group at position 4 and oxo groups at positions 3, 7 and 11 (the 4alpha,5alpha stereoisomer). Isolated from Antrodia cinnamomea and Antrodia camphorata, it exhibits cytotoxic and anti-inflammatory activity.		3.135011-oxo steroid;
3-oxo steroid;
7-oxo steroid;
ergostanoid;
monocarboxylic acid;
steroid acid		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
antrocamphin a
antrocamphin A: an NSAID isolated from Taiwanofungus camphoratus; structure in first source. antrocapmphin A : A methoxybenzene that is 1,2,5-trimethoxy-3-methylbenzene substituted by a 3-methylbut-3-en-1-yn-1-yl group at position 4. It is isolated from Antrodia camphorata and exhibits anti-inflammatory activity.		2.0610methoxybenzenesanti-inflammatory agent;
metabolite
4,7-dimethoxy-5-methyl-1,3-benzodioxole
4,7-dimethoxy-5-methyl-1,3-benzodioxole: has antineoplastic activity; isolated from Antrodia camphorata; structure in first source		2.0610
3alpha,12alpha-dihydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid
zhankuic acid C: isolated from Antrodia cinnamomea; structure given in first source. zhankuic acid C : A steroid acid that is ergosta-8,24(28)-dien-26-oic acid substituted by hydroxy groups at positions 3 and 12, a methyl group at position 4 and oxo groups at positions 7 and 11 (the 3alpha,4alpha,5alpha,12alpha stereoisomer). Isolated from Antrodia cinnamomea and Antrodia camphorata, it exhibits antineoplastic activity.		3.135011-oxo steroid;
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7-oxo steroid;
monocarboxylic acid;
secondary alpha-hydroxy ketone;
steroid acid		antineoplastic agent;
metabolite
antcin k
antcin K: has antineoplastic activity; isolated from Antrodia cinnamomea; structure in first source		2.7330bile acidmetabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9810
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		01.9810
Muscle Relaxation
That phase of a muscle twitch during which a muscle returns to a resting position.		01.9810
Contact Dermatitis
[description not available]		02.1110
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		02.1110