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

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

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. [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	10004842
CHEMBL ID	1644789
CHEBI ID	66503
SCHEMBL ID	17368945
MeSH ID	M0258412

Synonym
bdbm50334061
zhankuic acid a
chebi:66503 ,
CHEMBL1644789 ,
4alpha-methylergosta-8,24(28)-dien-3,7,11-trione-26-oic acid
(4alpha,5alpha)-4-methyl-3,7,11-trioxoergosta-8,24(28)-dien-26-oic acid
173327-15-6
SCHEMBL17368945
DTXSID60434004
(6r)-2-methyl-3-methylidene-6-[(4s,5s,10s,13r,14r,17r)-4,10,13-trimethyl-3,7,11-trioxo-1,2,4,5,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]heptanoic acid
Q27135108

Role	Description
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent	Any compound that has anti-inflammatory effects.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
3-oxo steroid	Any oxo steroid where an oxo substituent is located at position 3.
7-oxo steroid	Any oxo steroid carrying an oxo group at position 7.
11-oxo steroid	Any oxo steroid that has an oxo substituent at position 11.
steroid acid	Any steroid substituted by at least one carboxy group.
monocarboxylic acid	An oxoacid containing a single carboxy group.
ergostanoid
[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	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Nitric oxide synthase, inducible	Mus musculus (house mouse)	IC50 (µMol)	3.6000	0.0010	3.3911	9.6000	AID552870
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay ID	Title	Year	Journal	Article
AID550016	Antiinflammatory activity in mouse BV2 cells assessed as inhibition of NOX-dependent ROS production up to 50 uM	2010	Journal 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.
AID552864	Cytotoxicity against human DaOY cells after 3 days by MTT assay	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID550015	Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced iNOS-dependent nitrite production after 24 hrs by Griess method	2010	Journal 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.
AID1247996	Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced IL-12 production at 50 ug/ml	2015	Bioorganic & 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.
AID360214	Cytotoxicity against mouse P388 cells after 72 hrs	1995	Journal of natural products, Nov, Volume: 58, Issue:11	New steroid acids from Antrodia cinnamomea, a fungal parasite of Cinnamomum micranthum.
AID552868	Inhibition of mouse NOX activity in NADPH-induced mouse BV2 microglial cells assessed as NO production	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID552867	Cytotoxicity against human HeLa cells after 3 days by MTT assay	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID552869	Inhibition of NOX in fMLP-induced PMN cells assessed as NO production	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID552866	Cytotoxicity against human MCF7 cells after 3 days by MTT assay	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID1247995	Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced IL-6 production at 50 ug/ml	2015	Bioorganic & 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.
AID552870	Inhibition of iNOS in mouse BV2 microglial cells assessed as NO production	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID550014	Cytotoxicity against human KBVIN cells after 3 days by sulforhodamine B assay	2010	Journal 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.
AID1247994	Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced TNF-alpha production at 50 ug/ml	2015	Bioorganic & 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.
AID550013	Cytotoxicity against human KB cells after 3 days by sulforhodamine B assay	2010	Journal 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.
AID1247997	Immunosuppressive activity in mouse bone marrow-derived dendritic cells assessed as decrease in LPS-induced RANTES production at 50 ug/ml	2015	Bioorganic & 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.
AID552865	Cytotoxicity against human Hep2 cells after 3 days by MTT assay	2011	Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1	Biologically active constituents from the fruiting body of Taiwanofungus camphoratus.
AID550017	Antiinflammatory activity in human PMNC cells assessed as inhibition of fMLP-induced NOX-dependent ROS production up to 50 uM	2010	Journal 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (10.00)	18.2507
2000's	1 (10.00)	29.6817
2010's	8 (80.00)	24.3611
2020's	0 (0.00)	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	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	10 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.46	2	organic 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.	2.06	1	mitomycin	alkylating agent; antineoplastic agent
cordycepin [no description available]	2.07	1	3'-deoxyribonucleoside; adenosines	antimetabolite; nucleoside antibiotic
etoposide [no description available]	2.05	1	beta-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.	2.46	2	alpha-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.	2.06	1	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
lanosterol [no description available]	2.07	1	14alpha-methyl steroid; 3beta-sterol; tetracyclic triterpenoid	bacterial metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ergosterol [no description available]	3.66	9	3beta-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.	2.46	2	3beta-sterol; ergostanoid; organic peroxide; phytosterols	antimycobacterial drug; antineoplastic agent; metabolite; trypanocidal drug
dehydroeburicoic acid dehydroeburicoic acid: structure in first source	2.07	1	bile 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.	2.06	1	methoxybenzenes	anti-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	2.06	1
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.	3.29	6	11-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	2.73	3	bile acid	metabolite
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.	3.13	5	11-oxo steroid; 3alpha-hydroxy steroid; 7-oxo steroid; monocarboxylic acid; steroid acid	antineoplastic agent; cholinergic antagonist; metabolite; serotonergic antagonist
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	2.1	1

Condition	Relationship Strength	Studies
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.98	1
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.	1.98	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	1.98	1
Contact Dermatitis [description not available]	2.11	1
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.	2.11	1
Infections, Salmonella [description not available]	2.1	1
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	2.1	1
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	2.1	1
Acute Liver Injury, Drug-Induced [description not available]	2.1	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.1	1
Lung Adenocarcinoma [description not available]	2.07	1
Adenocarcinoma, Basal Cell [description not available]	2.07	1
Cancer of Lung [description not available]	2.07	1
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.07	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.07	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.07	1
Leucocythaemia [description not available]	2.07	1
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)	2.07	1

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

Description

Cross-References

Synonyms (11)

Roles (3)

Drug Classes (6)

Protein Targets (1)

Inhibition Measurements

Bioassays (17)

Research

Studies (10)

Market Indicators

Research Demand Index: 12.70

Study Types

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

Description

Cross-References

Synonyms (11)

Roles (3)

Drug Classes (6)

Protein Targets (1)

Inhibition Measurements

Bioassays (17)

Research

Studies (10)

Market Indicators

Research Demand Index: 12.70

Study Types

Related Drugs (16)

Related Conditions (18)