Compounds > 3alpha,12alpha-dihydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid
Page last updated: 2024-11-13

3alpha,12alpha-dihydroxy-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 C: isolated from Antrodia cinnamomea; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID53318662
CHEBI ID66505
SCHEMBL ID17368931
MeSH IDM0258550

Synonyms (6)

Synonym
zhankuic acid c
chebi:66505 ,
(3alpha,4alpha,5alpha,12alpha)-3,12-dihydroxy-4-methyl-7,11-dioxoergosta-8,24(28)-dien-26-oic acid
3alpha,12alpha-dihydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid
SCHEMBL17368931
Q27135110
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

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.
[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 (7)

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.
steroid acidAny steroid substituted by at least one carboxy group.
3alpha-hydroxy steroidA 3-hydroxy steroid in which the 3-hydroxy substituent is in the alpha-position.
12alpha-hydroxy steroid
monocarboxylic acidAn oxoacid containing a single carboxy group.
secondary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
[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)16.20000.00103.39119.6000AID552870
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
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.
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.
AID1248000Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced IL-12 production2015Bioorganic & 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.
AID1248015Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD40 expression by measuring mean fluorescence intensity at 100 ug/ml by flow cytometry (Rvb = 17.06 No_unit)2015Bioorganic & 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.
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.
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.
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.
AID1248006Immunosuppressive activity in DNFB-sensitized mouse assessed as inhibition of contact hypersensitivity response by measuring decrease in thickness of ear measured after 6 days2015Bioorganic & 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.
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.
AID1248007Immunosuppressive activity in DNFB-sensitized mouse assessed as decrease in T(CD3+) cells in ear by immunohistochemical analysis2015Bioorganic & 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.
AID1248003Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD80 expression by flow cytometry2015Bioorganic & 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.
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.
AID1248011Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD80 expression by measuring mean fluorescence intensity at 50 ug/ml by flow cytometry (Rvb = 47.09 No_unit)2015Bioorganic & 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.
AID1247999Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced IL-6 production2015Bioorganic & 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.
AID1248016Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in MHC-2 expression by measuring mean fluorescence intensity at 100 ug/ml by flow cytometry (Rvb = 61.23 No_unit)2015Bioorganic & 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.
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.
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.
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.
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.
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.
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.
AID1248008Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD80 expression by measuring mean fluorescence intensity at 25 ug/ml by flow cytometry (Rvb = 47.09 No_unit)2015Bioorganic & 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.
AID1248010Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in MHC-2 expression by measuring mean fluorescence intensity at 25 ug/ml by flow cytometry (Rvb = 61.23 No_unit)2015Bioorganic & 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.
AID1248002Cytotoxicity against mouse bone marrow-derived dendritic cells at 12.5 to 100 ug/ml after 24 hrs by CCK-8 assay2015Bioorganic & 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.
AID1247998Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced TNF-alpha production2015Bioorganic & 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.
AID1248001Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced RANTES production2015Bioorganic & 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.
AID1248004Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD40 expression by flow cytometry2015Bioorganic & 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.
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.
AID1248012Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD40 expression by measuring mean fluorescence intensity at 50 ug/ml by flow cytometry (Rvb = 17.06 No_unit)2015Bioorganic & 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.
AID1248013Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in MHC-2 expression by measuring mean fluorescence intensity at 50 ug/ml by flow cytometry (Rvb = 61.23 No_unit)2015Bioorganic & 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.
AID1248009Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD40 expression by measuring mean fluorescence intensity at 25 ug/ml by flow cytometry (Rvb = 17.06 No_unit)2015Bioorganic & 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.
AID1248005Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in MHC-2 expression by flow cytometry2015Bioorganic & 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.
AID1248014Inhibition of LPS-induced mouse bone marrow derived Dendritic cell maturation assessed as decrease in CD80 expression by measuring mean fluorescence intensity at 100 ug/ml by flow cytometry (Rvb = 47.09 No_unit)2015Bioorganic & 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's1 (16.67)29.6817
2010's4 (66.67)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: 12.82

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 Index12.82 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.82)

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%
Other6 (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
lanosterol
[no description available]		2.071014alpha-methyl steroid;
3beta-sterol;
tetracyclic triterpenoid		bacterial metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
ergosterol
[no description available]		3.29603beta-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.		3.296011-oxo steroid;
3-oxo steroid;
7-oxo steroid;
ergostanoid;
monocarboxylic acid;
steroid acid		anti-inflammatory agent;
antineoplastic agent;
plant metabolite
dehydroeburicoic acid
dehydroeburicoic acid: structure in first source		2.0710bile acid
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
antcin k
antcin K: has antineoplastic activity; isolated from Antrodia cinnamomea; structure in first source		2.7330bile acidmetabolite
3alpha-hydroxy-4alpha-methylergosta-8,24(28)-dien-7,11-dione-26-oic acid
zhankuic acid B: isolated from Antrodia cinnamomea; structure in first source. 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.		3.135011-oxo steroid;
3alpha-hydroxy steroid;
7-oxo steroid;
monocarboxylic acid;
steroid acid		antineoplastic agent;
cholinergic antagonist;
metabolite;
serotonergic antagonist
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
Leucocythaemia
[description not available]		02.0710
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.0710