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

copalic acid

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

Description

copalic acid: a trypanocidal agent isolated from Aristolochia cymbifera; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
AristolochiagenusA plant genus of the family ARISTOLOCHIACEAE. Species of this genus have been used in traditional medicine but they contain aristolochic acid which is associated with nephropathy. These are sometimes called 'snakeroot' but that name is also used with a number of other plants such as POLYGALA; SANICULA; ASARUM; ARISTOLOCHIA; AGERATINA; and others.[MeSH]AristolochiaceaeA plant family of the order Aristolochiales subclass Magnoliidae class Magnoliopsida. They are mostly tropical woody vines and a few temperate-zone species. The flowers are 3-parted; some species lack petals while others are large and foul smelling.[MeSH]

Cross-References

ID SourceID
PubMed CID11162521
CHEMBL ID102201
CHEBI ID170112
MeSH IDM0555533

Synonyms (13)

Synonym
CHEMBL102201
(e)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-enoic acid
CHEBI:170112
copalic acid
inchi=1/c20h32o2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h13,16-17h,2,6-12h2,1,3-5h3,(h,21,22)/b14-13+/t16-,17-,20+/m1/s
ent-copalic acid
(e)-5-[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylene-decalin-1-yl]-3-methyl-pent-2-enoic acid
DTXSID701316809
copalic acid, (-)-
2-pentenoic acid, 5-(decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)-3-methyl-, [1r-[1alpha(e),4abeta,8aalpha]]-
(2e)-5-[(1r,4ar,8ar)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]-3-methyl-2-pentenoic acid
6LTQ2LP2NB
2-pentenoic acid, 5-[(1r,4ar,8ar)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]-3-methyl-, (2e)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diterpenoidAny terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl 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]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID669311Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower left quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 2.40%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669300Cytotoxicity against monkey LLC-MK2 cells after 96 hrs by sulforhodamine B assay2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669310Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper left quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 3.76%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669297Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes after 96 hrs by neubauer chamber2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669298Antitrypanosomal activity against Trypanosoma cruzi Y trymastigotes infected in monkey LLC-MK2 cells after 24 hrs by Brenner counter method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669307Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower left quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 89.35%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID1471083Inhibition of heat shock protein 27 in human LNCaP cells assessed as decrease in AR protein level at 20 uM after 48 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein.
AID376663Inhibition of AChE2006Journal of natural products, May, Volume: 69, Issue:5
Bioactive diterpenes from the fruits of Detarium microcarpum.
AID669309Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper right quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 1.40%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669296Antitrypanosomal activity against Trypanosoma cruzi Y infected in monkey LLC-MK2 cells assessed as reduction in number of amastigotes after 96 hrs by Geimsa staining method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669312Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower right quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 1.12%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669306Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as lipid peroxidation at 400 uM after 6 hrs2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669314Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper left quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 1.54%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID1471082Inhibition of heat shock protein 27 in human LNCaP cells assessed as decrease in AR protein level at 200 uM after 48 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein.
AID669313Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper right quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 94.94%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669301Toxicity in human RBC assessed as hemolysis after 3 hrs2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669302Selectivity ratio of CC50 for monkey LLC-MK2 cells to IC50 for Trypanosoma cruzi Y amastigotes2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669299Antitrypanosomal activity against Trypanosoma cruzi Y amastigotes infected in monkey LLC-MK2 cells after 96 hrs by Geimsa staining method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669308Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower right quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 5.41%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID376662Antifungal activity against Cladosporium cucumerinum after 3 days2006Journal of natural products, May, Volume: 69, Issue:5
Bioactive diterpenes from the fruits of Detarium microcarpum.
AID669317Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as pronounced swelling of mitochondria at compound IC50 concentration after 96 hrs by transmission electron microscopic analysis2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (8.33)29.6817
2010's11 (91.67)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: 42.69

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

MetricThis Compound (vs All)
Research Demand Index42.69 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index120.17 (26.88)
Search Engine Supply Index4.00 (0.95)

This Compound (42.69)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
miconazole
Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.		2.0310dichlorobenzene;
ether;
imidazoles
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.0310benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
benzonidazole
benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.		2.0710C-nitro compound;
imidazoles;
monocarboxylic acid amide		antiprotozoal drug
kaurenoic acid
[no description available]		2.0710ent-kaurane diterpenoidanti-HIV-1 agent;
antineoplastic agent;
plant metabolite
sclareol
sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.		2.0610labdane diterpenoidantifungal agent;
antimicrobial agent;
apoptosis inducer;
fragrance;
plant metabolite
kusunokinin
kusunokinin: a trypanocidal agent isolated from Aristolochia cymbifera; structure in first source		2.0510
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.0510
sesquiterpenes
[no description available]		2.0610
kaurenoic acid
kaurenoic acid: isolated from leaves of Montanoa tomentosa; structure given in first source. ent-kaur-16-en-19-oic acid : An ent-kaurane diterpenoid that is ent-kauran-19-oic acid in which a double bond is present at position 16(17); exhibits anticancer and anti-HIV 1 activity.		2.1110
manool
manool: structure in first source. manool : A labdane diterpenoid in which the labdane skeleton has double bonds at positions 8(17) and 14 and carries an R-hydroxy group at position 13.		2.0610labdane diterpenoid;
tertiary alcohol		antibacterial agent;
antineoplastic agent;
plant metabolite
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		2.0710antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
caryophyllene
(-)-beta-caryophyllene : A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.. beta-caryophyllene : A sesquiterpene with a [7.2.0]-bicyclic structure comprising fused 9- and 4-membered rings, with a trans-ring junction, a trans-double bond between the 4- and 5-positions of the 9-membered ring, a methylidene group at position 9, and methyl groups at positions 3, 11, and 11. The most commonly occurring form is the (1R,9S)-(-)-enantiomer, which is found in many essential oils, particularly clove oil.. cannabinoid : A diverse group of pharmacologically active secondary metabolite characteristic to Cannabis plant as well as produced naturally in the body by humans and animals. Cannabinoids contain oxygen as a part of the heterocyclic ring or in the form of various functional groups. They are subdivided on the basis of their origin.		2.0710beta-caryophyllenefragrance;
insect attractant;
metabolite;
non-steroidal anti-inflammatory drug
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Prostate
[description not available]		02.1510
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.1510
Aberrant Crypt Foci
Clusters of colonic crypts that appear different from the surrounding mucosa when visualized after staining. They are of interest as putative precursors to colorectal adenomas and potential biomarkers for colorectal carcinoma.		02.1510
Cancer of Colon
[description not available]		02.1510
Chromosome-Defective Micronuclei
[description not available]		02.1510
Colonic Neoplasms
Tumors or cancer of the COLON.		02.1510
Mastitis, Bovine
INFLAMMATION of the UDDER in cows.		02.0810
American Trypanosomiasis
[description not available]		02.0510
Chagas Disease
Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.		02.0510
Caries, Dental
[description not available]		02.0610
Dental Caries
Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.		02.0610
Pericementitis
[description not available]		02.0610
Periodontitis
Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)		02.0610
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)		02.0810