Compounds > ovatodiolide
Page last updated: 2024-12-11

ovatodiolide

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

Description

ovatodiolide: from Anisomeles indica; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6451060
CHEMBL ID470287
SCHEMBL ID14704328
SCHEMBL ID16470767
MeSH IDM0395332

Synonyms (11)

Synonym
3,7,11,15(17)-cembratetraene-16,2:19,6-diolide
(3e,12e)-3,12-dimethyl-8-methylene-6,18-dioxa-tricyclo[14.2.1.0.5,9]nonadeca-3,12,16(19)-triene-7,17-dione
nsc 156130
ovatodiolide
3484-37-5
CHEMBL470287
641ilf0qgz ,
unii-641ilf0qgz
(3e,12e)-3,12-dimethyl-8-methylene-6,18-dioxa-tricyclo(14.2.1.0.5,9)nonadeca-3,12,16(19)-triene-7,17-dione
SCHEMBL14704328
SCHEMBL16470767

Research Excerpts

Overview

Ovatodiolide (Ova) is a macrocyclic diterpenoid compound isolated from Anisomeles indica (L.) Kuntze with anti-cancer activity.

ExcerptReferenceRelevance
"Ovatodiolide (Ova) is a macrocyclic diterpenoid compound isolated from Anisomeles indica (L.) Kuntze with anti-cancer activity."( Ovatodiolide Inhibits Breast Cancer Stem/Progenitor Cells through SMURF2-Mediated Downregulation of Hsp27.
Chang, WW; Chang-Chien, J; Chi, WY; Lee, HT; Lu, KT; Tzeng, YM; Wang, BY; Yang, JJ, 2016)		2.6

Treatment

Ovatodiolide treatment suppressed YAP1 oncogenic pathways to inhibit colon tumorigenesis and M2 TAM generation both in vitro and in vivo. Treatment also induced apoptosis, as indicated by caspase activation, DNA fragmentation, and poly (ADP-ribose) polymerase (PARP) cleavage.

ExcerptReferenceRelevance
"Ovatodiolide treatment alone and in combination with 5-FU significantly suppressed in vivo tumorigenesis and less TAM infiltration in CT26 syngeneic mouse model."( Ovatodiolide suppresses colon tumorigenesis and prevents polarization of M2 tumor-associated macrophages through YAP oncogenic pathways.
Hsiao, M; Huang, YJ; Huynh, TT; Meng, TC; Tzeng, YM; Wei, PL; Whang-Peng, J; Wu, AT; Yang, CK; Yen, Y, 2017)		2.62
"Ovatodiolide treatment suppressed YAP1 oncogenic pathways to inhibit colon tumorigenesis and M2 TAM generation both in vitro and in vivo."( Ovatodiolide suppresses colon tumorigenesis and prevents polarization of M2 tumor-associated macrophages through YAP oncogenic pathways.
Hsiao, M; Huang, YJ; Huynh, TT; Meng, TC; Tzeng, YM; Wei, PL; Whang-Peng, J; Wu, AT; Yang, CK; Yen, Y, 2017)		2.62
"Ovatodiolide treatment also induced apoptosis, as indicated by caspase activation, DNA fragmentation, and poly (ADP-ribose) polymerase (PARP) cleavage."( The natural diterpenoid ovatodiolide induces cell cycle arrest and apoptosis in human oral squamous cell carcinoma Ca9-22 cells.
Chang, FR; Hou, YY; Hwang, YC; Wu, CC; Wu, ML; Wu, YC, 2009)		1.38

Toxicity

ExcerptReferenceRelevance
" Doxorubicin (Doxo), a class I anthracycline and first-line anticancer agent, effective against a wide spectrum of neoplasms including breast carcinoma, is associated with several cumulative dose-dependent adverse effects, including cardiomyopathy, typhilitis, and acute myelotoxicity."( Ovatodiolide sensitizes aggressive breast cancer cells to doxorubicin, eliminates their cancer stem cell-like phenotype, and reduces doxorubicin-associated toxicity.
Bamodu, OA; Chao, TY; Huang, WC; Tzeng, DT; Wang, LS; Wu, A; Yeh, CT, 2015)		1.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID343506Cytotoxicity against human A549 cells after 3 days by MTT assay2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
AID1235532Inhibition of hedgehog signaling pathway in human HaCaT cells assessed as GLI1-mediated transcriptional activity after 12 hrs by luciferase assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID1235541Inhibition of hedgehog signaling pathway in human DU145 cells assessed as reduction of BCL2 expression at 7 to 13.9 uM after 12 hrs by Western blotting2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID1235534Cytotoxicity against Hh signaling abnormally activated human DU145 cells after 24 hrs by fluorometric microculture assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID343509Inhibition of collagen-induced human platelet aggregation by light transmission aggregometer2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
AID471320Cytotoxicity against human K562 cells after 48 hrs2009Journal of natural products, Oct, Volume: 72, Issue:10
ent-Kaurane and cembrane diterpenoids from Isodon sculponeatus and their cytotoxicity.
AID343508Cytotoxicity against human MCF7 cells after 3 days by MTT assay2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
AID1235538Inhibition of hedgehog signaling pathway in human HaCaT cells assessed as reduction of BCL2 expression after 12 hrs by Western blotting2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID1235535Cytotoxicity against mouse C3H10T1/2 cells after 24 hrs by fluorometric microculture assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID471322Cytotoxicity against human HepG2 cells after 48 hrs2009Journal of natural products, Oct, Volume: 72, Issue:10
ent-Kaurane and cembrane diterpenoids from Isodon sculponeatus and their cytotoxicity.
AID1235540Inhibition of GLI1-DNA (unknown origin) complex formation at 15 to 150 uM after 20 mins by electrophoretic mobility shift assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID1235533Cytotoxicity against Hh signaling abnormally activated human PANC1 cells after 24 hrs by fluorometric microculture assay2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID1235537Inhibition of hedgehog signaling pathway in human HaCaT cells assessed as reduction of BCL2 expression at 7.6 uM after 12 hrs by Western blotting2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Hedgehog inhibitors from Artocarpus communis and Hyptis suaveolens.
AID343505Cytotoxicity against human Hep3B cells after 3 days by MTT assay2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
AID343510Inhibition of thrombin-induced human platelet aggregation by light transmission aggregometer2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
AID343507Cytotoxicity against human MDA-MB-231 cells after 3 days by MTT assay2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
AID471321Cytotoxicity against human A549 cells after 48 hrs2009Journal of natural products, Oct, Volume: 72, Issue:10
ent-Kaurane and cembrane diterpenoids from Isodon sculponeatus and their cytotoxicity.
AID343504Cytotoxicity against human HepG2 cells after 3 days by MTT assay2008Journal of natural products, Jul, Volume: 71, Issue:7
Bioactive cembrane diterpenoids of Anisomeles indica.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (13.79)29.6817
2010's17 (58.62)24.3611
2020's8 (27.59)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.41

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 Index25.41 (24.57)
Research Supply Index3.47 (2.92)
Research Growth Index5.54 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.41)

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%
Other31 (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.		2.0710alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
niacinamide
nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.		2.1710pyridine alkaloid;
pyridinecarboxamide;
vitamin B3		anti-inflammatory agent;
antioxidant;
cofactor;
EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
Escherichia coli metabolite;
geroprotector;
human urinary metabolite;
metabolite;
mouse metabolite;
neuroprotective agent;
Saccharomyces cerevisiae metabolite;
Sir2 inhibitor
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		2.0410benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
temozolomide
[no description available]		7.2110imidazotetrazine;
monocarboxylic acid amide;
triazene derivative		alkylating agent;
antineoplastic agent;
prodrug
thiazoles
[no description available]		2.05101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
hesperidin
Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.		2.31103'-hydroxyflavanones;
4'-methoxyflavanones;
dihydroxyflavanone;
disaccharide derivative;
flavanone glycoside;
monomethoxyflavanone;
rutinoside		mutagen
thiazolyl blue
thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.		2.0510organic bromide saltcolorimetric reagent;
dye
hesperetin
[no description available]		2.31103'-hydroxyflavanones;
4'-methoxyflavanones;
monomethoxyflavanone;
trihydroxyflavanone		antineoplastic agent;
antioxidant;
plant metabolite
fibrinogen
Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.		2.3110iditolfungal metabolite
sorafenib
[no description available]		2.6920(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
phenylureas;
pyridinecarboxamide		angiogenesis inhibitor;
anticoronaviral agent;
antineoplastic agent;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
ferroptosis inducer;
tyrosine kinase inhibitor
enmein
enmein: structure		2.0510delta-lactonemetabolite
sesquiterpenes
[no description available]		2.610
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		2.0810
mimulone
mimulone: structure in first source		2.1110
nodosin
nodosin: has anti-inflammatory activity; isolated from Isodon serra; structure in first source		2.0510delta-lactonemetabolite
interleukin-8
Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.		2.0810
antcin k
antcin K: has antineoplastic activity; isolated from Antrodia cinnamomea; structure in first source		7.610bile acidmetabolite
antrocin
antrocin: from Antrodia camphorata; structure in first source		7.610
transforming growth factor beta
Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.		2.610
ConditionIndicatedRelationship StrengthStudiesTrials
Cerebral Infarction, Middle Cerebral Artery
[description not available]		02.4110
Cerebral Ischemia
[description not available]		02.4110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		03.2750
Injury, Ischemia-Reperfusion
[description not available]		02.4110
Brain Ischemia
Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.		02.4110
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		02.4110
Infarction, Middle Cerebral Artery
NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.		02.4110
Cardiovascular Stroke
[description not available]		02.4110
Myocardial Infarction
NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).		07.4110
Hepatocellular Carcinoma
[description not available]		02.9330
Cancer of Liver
[description not available]		02.9330
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.9330
Liver Neoplasms
Tumors or cancer of the LIVER.		02.9330
2019 Novel Coronavirus Disease
[description not available]		02.610
Alveolitis, Fibrosing
[description not available]		02.610
Pulmonary Fibrosis
A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.		07.610
Cardiovascular Diseases
Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.		02.610
Carcinogenesis
The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.		07.5920
Bladder Cancer
[description not available]		02.2510
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		02.2510
Autoimmune Chronic Hepatitis
[description not available]		02.2510
Hepatitis, Autoimmune
A chronic self-perpetuating hepatocellular INFLAMMATION of unknown cause, usually with HYPERGAMMAGLOBULINEMIA and serum AUTOANTIBODIES.		02.2510
Astrocytoma, Grade IV
[description not available]		02.6620
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.		07.6620
Asthma, Bronchial
[description not available]		02.1510
Asthma
A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).		07.1510
Cell Transformation, Neoplastic
Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.		02.1710
Cancer of Nasopharynx
[description not available]		02.2110
Nasopharyngeal Neoplasms
Tumors or cancer of the NASOPHARYNX.		02.2110
Nasopharyngeal Carcinoma
A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.		07.2110
Metastase
[description not available]		02.5220
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.5220
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		02.1110
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		02.1110
Breast Cancer
[description not available]		02.4920
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.4920
Cancer of Colon
[description not available]		02.1510
Colonic Neoplasms
Tumors or cancer of the COLON.		02.1510
Carcinoma, Epidermoid
[description not available]		02.0510
Cancer of Mouth
[description not available]		02.0510
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		02.0510
Mouth Neoplasms
Tumors or cancer of the MOUTH.		02.0510
Innate Inflammatory Response
[description not available]		02.0810
Infections, Helicobacter
[description not available]		02.0810
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.		02.0810
Helicobacter Infections
Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.		02.0810