2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid ethyl amide profile

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid ethyl amide: synthetic potential anticarcinogenic [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	44159258
CHEMBL ID	3105688
SCHEMBL ID	4243122
MeSH ID	M0508815

Synonym
cddo-ethyl amide
rta 405
2-cyano-3,12-dioxooleana-1,9(11)dien-28-oic acid-ethyl amide
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid ethyl amide
HY-12213
cddo-ea
CHEMBL3105688
SCHEMBL4243122
AC-36699
bdbm217380
cddo-ea, 3
cddo ethyl amide
932730-51-3
cddo ethyl amide;tp319;rta 405
(4as,6ar,6bs,8ar,12as,14ar,14bs)-11-cyano-n-ethyl-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxamide
tp319
A916298
MS-29625
AKOS040732763

Excerpt	Reference	Relevance
" However, increases in albuminuria, serum transaminase, and frequency of adverse events were noted."	( Analogs of bardoxolone methyl worsen diabetic nephropathy in rats with additional adverse effects. Abbate, M; Benigni, A; Carrara, F; Corna, D; Gaspari, F; Locatelli, M; Nava, V; Remuzzi, G; Sangalli, F; Zoja, C, 2013)	0.39

Excerpt	Reference	Relevance
" Therefore, the effects of the orally bioavailable synthetic triterpenoid 2-cyano-3,12-dioxooleana- 1,9(11)-dien-28-oate-ethyl amide (CDDO-EA, RTA 405), which has potent antioxidative and antiinflammatory properties, was evaluated in a chronic carbon tetrachloride (CCl(4))-induced model of liver cirrhosis and hepatocellular carcinoma (HCC)."	( The Synthetic Triterpenoid RTA 405 (CDDO-EA) Halts Progression of Liver Fibrosis and Reduces Hepatocellular Carcinoma Size Resulting in Increased Survival in an Experimental Model of Chronic Liver Injury. Cusimano, FA; Getachew, Y; Gopal, P; Reisman, SA; Shay, JW, 2016)	0.43

Excerpt	Relevance	Reference
" If mice were fed either the methyl ester or the ethyl amide derivative of the synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO-ME and CDDO-EA, respectively), beginning 1 week after dosing with carcinogen, the number, size, and severity of lung carcinomas were markedly reduced."	( The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice. Dmitrovsky, E; Gribble, GW; Honda, T; Liby, K; Risingsong, R; Royce, DB; Sporn, MB; Sporn, TA; Williams, CR; Yore, MM, 2007)	0.34

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Ghrelin O-acyltransferase	Mus musculus (house mouse)	IC50 (µMol)	0.3200	0.0350	0.1775	0.3200	AID1639666
Ghrelin O-acyltransferase	Homo sapiens (human)	IC50 (µMol)	8.0000	6.0000	7.5000	8.0000	AID1639664; AID1679014; AID1802486
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
peptide hormone processing	Ghrelin O-acyltransferase	Homo sapiens (human)
peptidyl-serine octanoylation	Ghrelin O-acyltransferase	Homo sapiens (human)
lipid modification	Ghrelin O-acyltransferase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
O-acyltransferase activity	Ghrelin O-acyltransferase	Homo sapiens (human)
acyltransferase activity, transferring groups other than amino-acyl groups	Ghrelin O-acyltransferase	Homo sapiens (human)
serine O-acyltransferase activity	Ghrelin O-acyltransferase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
endoplasmic reticulum	Ghrelin O-acyltransferase	Homo sapiens (human)
endoplasmic reticulum membrane	Ghrelin O-acyltransferase	Homo sapiens (human)
endoplasmic reticulum membrane	Ghrelin O-acyltransferase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1728762	Anti-necroptotic activity in human HT-29 cells assessed as inhibition of TNFalpha/SM-164/Z-VAD-fmk (TSZ)-induced necroptosis by measuring increase in cell viability measured after 12 hrs by celltiter-glo luminescent cell viability assay	2021	European journal of medicinal chemistry, Feb-15, Volume: 212	Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1064488	Antiproliferative activity against mouse PANC1343 cells at 300 to 1000 nM after 72 hrs by MTT assay	2014	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2	Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO).
AID1064491	Induction of Nrf2-mediated HO-1 expression in mouse RAW264.7 cells at 30 to 300 nM after 6 hrs by Western blot method	2014	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2	Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO).
AID1679014	Inhibition of human GOAT expressed in baculovirus infected sf9 insect cell membrane using GSSFLC-acrylodan and octanoyl-CoA as substrate preincubated for 30 mins followed by substrate addition and measured after 3 hrs by HPLC analysis	2020	RSC medicinal chemistry, Oct-01, Volume: 11, Issue:10	Recent progress in the discovery of ghrelin
AID1728767	Anti-necroptotic activity in mouse L929 cells assessed as inhibition of TNFalpha/Z-VAD-fmk (TZ)-induced necroptosis by measuring increase in cell viability measured after 12 hrs by celltiter-glo luminescent cell viability assay	2021	European journal of medicinal chemistry, Feb-15, Volume: 212	Discovery of bardoxolone derivatives as novel orally active necroptosis inhibitors.
AID1064492	Inhibition of IFN-gamma-induced nitric oxide production in mouse RAW264.7 cells at 30 nM after 24 hrs by Griess method	2014	Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2	Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO).
AID1802486	GOAT Activity Assay from Article 10.1021/acs.biochem.6b01008: \\Synthetic Triterpenoid Inhibition of Human Ghrelin O-Acyltransferase: The Involvement of a Functionally Required Cysteine Provides Mechanistic Insight into Ghrelin Acylation.\\	2017	Biochemistry, 02-21, Volume: 56, Issue:7	Synthetic Triterpenoid Inhibition of Human Ghrelin O-Acyltransferase: The Involvement of a Functionally Required Cysteine Provides Mechanistic Insight into Ghrelin Acylation.
[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	0 (0.00)	18.2507
2000's	2 (8.00)	29.6817
2010's	17 (68.00)	24.3611
2020's	6 (24.00)	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	1 (4.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (96.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
lg 100268 LG 100268: a retinoid X receptor (RXR) selective compound; structure given in first source	2.46	2
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	2.31	1	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
urethane [no description available]	2.44	2	carbamate ester	fungal metabolite; mutagen
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.15	1	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
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.	2.13	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
oleanolic acid [no description available]	4.5	21	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.15	1	cyclohexenone
vinyl carbamate vinyl carbamate: promutagen & more carcinogenic analog of ethyl carbamate (urethane); structure	2.44	2	carbamate ester
echinocystic acid [no description available]	2.31	1	triterpenoid
brusatol brusatol: quassinoid from B. javanica; structure	2.31	1	triterpenoid
cholest-4-en-3-one cholest-4-en-3-one : A cholestanoid that is cholest-4-ene substituted by an oxo group at position 3.	2.15	1	3-oxo-Delta(4) steroid; cholestanoid	human metabolite; plant metabolite
taraxerol taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.	2.15	1	pentacyclic triterpenoid; secondary alcohol	metabolite
androstan-3-one [no description available]	2.15	1
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.49	2	amino acid zwitterion; angiotensin II	human metabolite
Bardoxolone [no description available]	2.96	3	cyclohexenones
bardoxolone methyl methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate: structure in first source	3.59	8	cyclohexenones
dimethyl fumarate [no description available]	2.31	1	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
ramipril Ramipril: A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.. ramipril : A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.. quark : Quarks comprise one of two classes of the fundamental particles. Quarks possess fractional electric charges and are not observed in free state. The word "quark" first appears in James Joyce's Finnegans Wake and has been chosen by Murray Gell-Mann as a name for fundamental building blocks of particles.	2.08	1	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug
tanespimycin CP 127374: analog of herbimycin A	2.31	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound; secondary amino compound	antineoplastic agent; apoptosis inducer; Hsp90 inhibitor
agn 194204 AGN 194204: a retinoid X receptor ligand; structure in first source	2.05	1
1-(2-cyano-3,12-dioxooleana-1,9-dien-28-oyl) imidazole [no description available]	2.61	2
pazopanib pazopanib: a protein kinase inhibitor. pazopanib : A pyrimidine that is 5-(pyrimidin-2-yl}amino-2-methylbenzenesulfonamide substituted at position 4 by a (2,3-dimethylindazol-6-yl)(methyl)amino group. Used as its hydrochloride salt for treatment of kidney cancer.	2.31	1	aminopyrimidine; indazoles; sulfonamide	angiogenesis modulating agent; antineoplastic agent; tyrosine kinase inhibitor; vascular endothelial growth factor receptor antagonist
at 13387 (2,4-dihydroxy-5-isopropylphenyl)-(5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl)methanone: structure in first source. onalespib : A member of the class of isoindoles that is isoindole in which the amino group has been acylated by a 2,4-dihydroxy-5-isopropylbenzoyl group and in which position 5 of the isoidole moiety has been substituted by a (4-methylpiperazin-1-yl)methyl group. A second-generation Hsp90 inhibitor.	2.31	1	benzamides; isoindoles; N-alkylpiperazine; resorcinols; tertiary carboxamide	antineoplastic agent; Hsp90 inhibitor
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.	2.25	1
rta 408 omaveloxolone: has both anti-inflammatory and radiation protective activities	2.31	1

Condition	Relationship Strength	Studies
Inflammatory Response Syndrome, Systemic [description not available]	2.31	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.31	1
Systemic Inflammatory Response Syndrome A systemic inflammatory response to a variety of clinical insults, characterized by two or more of the following conditions: (1) fever	2.31	1
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.	2.31	1
Cognitive Decline [description not available]	2.41	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.47	7
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.41	1
Diabetes Mellitus, Adult-Onset [description not available]	2.58	2
Innate Inflammatory Response [description not available]	3.06	4
Insulin Sensitivity [description not available]	2.6	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.58	2
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.	3.06	4
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.6	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.58	2
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.	2.57	2
Hepatocellular Carcinoma [description not available]	2.25	1
Cancer of Liver [description not available]	2.25	1
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.	2.25	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.25	1
Cerebral Ischemia [description not available]	2.31	1
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.	2.31	1
Cerebral Malaria [description not available]	2.15	1
Alloxan Diabetes [description not available]	2.08	1
Benign Neoplasms [description not available]	2.11	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.11	1
Disease Exacerbation [description not available]	2.53	2
Cirrhoses, Experimental Liver [description not available]	2.13	1
Experimental Hepatoma [description not available]	2.13	1
Adenomatous Polyposis Coli, Familial [description not available]	2.13	1
Colorectal Cancer [description not available]	2.13	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.13	1
Adenomatous Polyposis Coli A polyposis syndrome due to an autosomal dominant mutation of the APC genes (GENES, APC) on CHROMOSOME 5. The syndrome is characterized by the development of hundreds of ADENOMATOUS POLYPS in the COLON and RECTUM of affected individuals by early adulthood.	2.13	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.13	1
Adenocarcinoma, Basal Cell [description not available]	2.44	2
Cancer of Lung [description not available]	2.44	2
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.44	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.44	2
Akinetic-Rigid Variant of Huntington Disease [description not available]	2.46	2
Huntington Disease A familial disorder inherited as an autosomal dominant trait and characterized by the onset of progressive CHOREA and DEMENTIA in the fourth or fifth decade of life. Common initial manifestations include paranoia; poor impulse control; DEPRESSION; HALLUCINATIONS; and DELUSIONS. Eventually intellectual impairment; loss of fine motor control; ATHETOSIS; and diffuse chorea involving axial and limb musculature develops, leading to a vegetative state within 10-15 years of disease onset. The juvenile variant has a more fulminant course including SEIZURES; ATAXIA; dementia; and chorea. (From Adams et al., Principles of Neurology, 6th ed, pp1060-4)	2.46	2
Cancer of Pancreas [description not available]	2.05	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.05	1
Degenerative Diseases, Central Nervous System [description not available]	2.06	1
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.06	1
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	2.06	1
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.06	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.08	1
Diabetic Glomerulosclerosis [description not available]	2.08	1
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.08	1

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid ethyl amide

Description

Cross-References

Synonyms (19)

Research Excerpts

Toxicity

Bioavailability

Dosage Studied

Protein Targets (2)

Inhibition Measurements

Biological Processes (3)

Molecular Functions (3)

Ceullar Components (2)

Bioassays (7)

Research

Studies (25)

Market Indicators

Research Demand Index: 11.75

Study Types

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid ethyl amide

Description

Cross-References

Synonyms (19)

Research Excerpts

Toxicity

Bioavailability

Dosage Studied

Protein Targets (2)

Inhibition Measurements

Biological Processes (3)

Molecular Functions (3)

Ceullar Components (2)

Bioassays (7)

Research

Studies (25)

Market Indicators

Research Demand Index: 11.75

Study Types

Related Drugs (25)

Related Conditions (48)