Compounds > dehydroeburicoic acid
Page last updated: 2024-11-12

dehydroeburicoic acid

Description

dehydroeburicoic acid: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID15250826
CHEMBL ID1744446
CHEBI ID80817
SCHEMBL ID18195826
MeSH IDM0543706

Synonyms (17)

Synonym
dehydroeburicoic acid
C16950
dehydroeburicoicacid
chebi:80817 ,
CHEMBL1744446
AC-34636
6879-05-6
dehydrotrametenolicacid
SCHEMBL18195826
AKOS037514512
HY-N2490
Q27149860
(2r)-2-[(3s,5r,10s,13r,14r,17r)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
(2r)-2-[(3s,5r,10s,13r,14r,17r)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1h-cyclopenta [a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
CS-0022761
MS-28661
DTXSID501346470

Research Excerpts

Overview

Dehydroeburicoic acid (DeEA) is a triterpene purified from medicinal fungi such as Antrodia camphorate. It is known to exert cytotoxic effects against several types of cancer cells.

ExcerptReferenceRelevance
"Dehydroeburicoic acid (DeEA) is a triterpene purified from medicinal fungi such as Antrodia camphorate, the crude extract of which is known to exert cytotoxic effects against several types of cancer cells. "( Dehydroeburicoic acid induces calcium- and calpain-dependent necrosis in human U87MG glioblastomas.
Chen, SJ; Deng, JY; Hsueh, CW; Jeng, CJ; Jow, GM, 2009)		3.24
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
bile acidAny member of a group of hydroxy-5beta-cholanic acids occuring in bile, where they are present as the sodium salts of their amides with glycine or taurine. In mammals bile acids almost invariably have 5beta-configuration.
[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]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID288566Inhibition of TPA-induced Epstein-Barr virus early antigen activation in Raji cells at 1000 mol ratio/32 pmol TPA relative to control2007Journal of natural products, Jun, Volume: 70, Issue:6
Triterpene acids from Poria cocos and their anti-tumor-promoting effects.
AID1546666Cytotoxicity against human U251 cells incubated for 24 hrs by MTT assay2020Journal of natural products, 01-24, Volume: 83, Issue:1
Antcamphorols A-K, Cytotoxic and ROS Scavenging Triterpenoids from
AID1546668Cytotoxicity against human SW480 cells incubated for 24 hrs by MTT assay2020Journal of natural products, 01-24, Volume: 83, Issue:1
Antcamphorols A-K, Cytotoxic and ROS Scavenging Triterpenoids from
AID1427863Antiproliferative activity against human CCRF-CEM cells after 72 hrs by MTT assay2016Journal of natural products, 11-23, Volume: 79, Issue:11
Cytotoxic Lanostanoids from Poria cocos.
AID288570Cell viability of Raji cells2007Journal of natural products, Jun, Volume: 70, Issue:6
Triterpene acids from Poria cocos and their anti-tumor-promoting effects.
AID288568Inhibition of TPA-induced Epstein-Barr virus early antigen activation in Raji cells at 100 mol ratio/32 pmol TPA relative to control2007Journal of natural products, Jun, Volume: 70, Issue:6
Triterpene acids from Poria cocos and their anti-tumor-promoting effects.
AID1546669Cytotoxicity against human L02 cells incubated for 24 hrs by MTT assay2020Journal of natural products, 01-24, Volume: 83, Issue:1
Antcamphorols A-K, Cytotoxic and ROS Scavenging Triterpenoids from
AID289114Inhibition of fMLP-induced superoxide production in human neutrophils2007Journal of natural products, Jun, Volume: 70, Issue:6
Anti-inflammatory benzenoids from Antrodia camphorata.
AID288569Inhibition of TPA-induced Epstein-Barr virus early antigen activation in Raji cells at 10 mol ratio/32 pmol TPA relative to control2007Journal of natural products, Jun, Volume: 70, Issue:6
Triterpene acids from Poria cocos and their anti-tumor-promoting effects.
AID288567Inhibition of TPA-induced Epstein-Barr virus early antigen activation in Raji cells at 500 mol ratio/32 pmol TPA relative to control2007Journal of natural products, Jun, Volume: 70, Issue:6
Triterpene acids from Poria cocos and their anti-tumor-promoting effects.
AID1546667Cytotoxicity against human MCF7 cells incubated for 24 hrs by MTT assay2020Journal of natural products, 01-24, Volume: 83, Issue:1
Antcamphorols A-K, Cytotoxic and ROS Scavenging Triterpenoids from
AID1427865Antiproliferative activity against human K562 cells after 72 hrs by MTT assay2016Journal of natural products, 11-23, Volume: 79, Issue:11
Cytotoxic Lanostanoids from Poria cocos.
AID1064288Cytotoxicity against human HS68 cells at 25 to 200 uM after 48 hrs by SRB assay2014Journal of natural products, Jan-24, Volume: 77, Issue:1
Antcamphins A-L, ergostanoids from Antrodia camphorata.
AID1427862Antiproliferative activity against human MOLT4 cells after 72 hrs by MTT assay2016Journal of natural products, 11-23, Volume: 79, Issue:11
Cytotoxic Lanostanoids from Poria cocos.
AID1546670Induction of ROS scavenging activity in HUVEC assessed as reduction in high glucose-induced intracellular ROS level at 20 uM incubated for 6 hrs by DCFH-DA/Hoechst 33342 staining based assay relative to control2020Journal of natural products, 01-24, Volume: 83, Issue:1
Antcamphorols A-K, Cytotoxic and ROS Scavenging Triterpenoids from
AID1427864Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay2016Journal of natural products, 11-23, Volume: 79, Issue:11
Cytotoxic Lanostanoids from Poria cocos.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (18.75)29.6817
2010's10 (62.50)24.3611
2020's3 (18.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.86

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.86 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.06 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.86)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.1710alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
ibuprofen
Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine		2.0310monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
environmental contaminant;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
radical scavenger;
xenobiotic
temozolomide
[no description available]		2.2510imidazotetrazine;
monocarboxylic acid amide;
triazene derivative		alkylating agent;
antineoplastic agent;
prodrug
carbon tetrachloride
Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.		2.0810chlorocarbon;
chloromethanes		hepatotoxic agent;
refrigerant
chloroform
Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.		2.1510chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant
irinotecan
[no description available]		2.2510carbamate ester;
delta-lactone;
N-acylpiperidine;
pyranoindolizinoquinoline;
ring assembly;
tertiary alcohol;
tertiary amino compound		antineoplastic agent;
apoptosis inducer;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
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.		2.0310benzodioxoles;
furofuran;
lignan		antineoplastic agent;
neuroprotective agent;
plant metabolite
eburicoic acid
eburicoic acid: structure		3.1950
friedelinol
friedelinol: isolated from seeds of Aster auriculatus Franch; structure given in first source; RN given refers to friedelanol (friedelinol), the (3alpha)-isomer		2.0310
dehydrotumulosic acid
dehydrotumulosic acid: inhibits phospholipase A2; isolated from Poria cocos; structure in first source		2.1710
lanosterol
[no description available]		3.9912014alpha-methyl steroid;
3beta-sterol;
tetracyclic triterpenoid		bacterial metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
ergosterol
[no description available]		2.51203beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite
sesquiterpenes
[no description available]		2.1110
beta carotene
beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.		2.0310carotenoid beta-end derivative;
cyclic carotene		antioxidant;
biological pigment;
cofactor;
ferroptosis inhibitor;
human metabolite;
mouse metabolite;
plant metabolite;
provitamin A
cholecalciferol
Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.		2.2510D3 vitamins;
hydroxy seco-steroid;
seco-cholestane;
secondary alcohol;
steroid hormone		geroprotector;
human metabolite
poricoic acid a
poricoic acid A: from Poria cocos (Polyporaceae); structure in first source. poricoic acid A : A tricyclic triterpenoid isolated from Poria cocos.		2.1310dicarboxylic acid;
secondary alcohol;
tricyclic triterpenoid		fungal metabolite
pachymic acid
pachymic acid: inhibits phospholipase A2; isolated from Poria cocos; structure in first source		3.0240triterpenoid
drimane
drimane: structure in first source		2.1110sesquiterpene;
terpenoid fundamental parent
beta-sitosterone
beta-sitosterone: from Torreya jackii		2.0310
polyporenic acid c
[no description available]		2.1310
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.		2.071011-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.		2.0310methoxybenzenesanti-inflammatory agent;
metabolite
calpain
Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.		7.0510
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		2.0310
antcin a
antcin A: from Antrodia camphorata, exerts anti-inflammatory effect via mimicking glucocorticoids; structure in first source		2.0310ergostanoidmetabolite
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.		2.071011-oxo steroid;
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7-oxo steroid;
monocarboxylic acid;
secondary alpha-hydroxy ketone;
steroid acid		antineoplastic agent;
metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Fatty Liver, Nonalcoholic
[description not available]		02.4110
Innate Inflammatory Response
[description not available]		02.4110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.4110
Non-alcoholic Fatty Liver Disease
Fatty liver finding without excessive ALCOHOL CONSUMPTION.		07.4110
Alcoholic Fatty Liver
[description not available]		07.3110
Anasarca
[description not available]		02.0810
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.0810
Acute Liver Injury, Drug-Induced
[description not available]		02.0810
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.5120
Acute Disease
Disease having a short and relatively severe course.		02.0810
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.		02.0810
Alloxan Diabetes
[description not available]		02.5220
Autoimmune Diabetes
[description not available]		02.1110
Diabetes Mellitus, Type 1
A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.		02.1110
Dyslipidemia
[description not available]		02.1310
Dyslipidemias
Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.		02.1310
Astrocytoma, Grade IV
[description not available]		02.0510
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		07.0510
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		07.0510
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)		07.0710
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