10-nitro-9,12-octadecadienoic acid profile

10-nitro-9,12-octadecadienoic acid, commonly known as **nitro-linoleic acid (NLA)**, is a derivative of the essential fatty acid linoleic acid. It's a molecule with a nitro group attached to the 10th carbon of the linoleic acid chain.

**Importance in research:**

NLA is gaining significant attention in research due to its potential biological activities, particularly in the fields of **cancer, inflammation, and cardiovascular disease**.

Here's why:

* **Anti-cancer activity:** Studies have shown that NLA can inhibit the growth of various cancer cell lines, both in vitro and in vivo. Its mechanism of action might involve the induction of apoptosis (programmed cell death) and the inhibition of angiogenesis (formation of new blood vessels).
* **Anti-inflammatory effects:** NLA has been shown to reduce inflammation by suppressing the production of pro-inflammatory cytokines and mediators. This could be beneficial in treating inflammatory diseases like arthritis.
* **Cardiovascular protection:** NLA has demonstrated the ability to lower blood pressure and reduce the risk of blood clots, suggesting potential benefits for cardiovascular health.
* **Neuroprotective properties:** Some studies suggest that NLA might protect against neuronal damage and improve cognitive function, although further research is needed.

**Challenges and future directions:**

Despite promising preclinical findings, the use of NLA in humans is still in its early stages. Research is ongoing to:

* **Understand the precise mechanisms of action of NLA:** More investigation is needed to clarify how this molecule exerts its various effects.
* **Develop safe and effective delivery methods:** NLA has poor bioavailability, meaning it's not easily absorbed by the body. Researchers are working on developing efficient delivery systems to enhance its therapeutic potential.
* **Conduct clinical trials:** Large-scale clinical trials are necessary to confirm the efficacy and safety of NLA in human patients.

Overall, 10-nitro-9,12-octadecadienoic acid holds significant promise as a potential therapeutic agent in various disease areas. However, more research is needed before it can be translated into clinical applications.

10-nitro-9,12-octadecadienoic acid: a nitric oxide donor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	5282259
CHEBI ID	34125
SCHEMBL ID	2370110
MeSH ID	M0486718

Synonym
10-nitro-9-cis,12-cis-octadecadienoic acid
LMFA01120001
10-nitro,9z,12z-octadecadienoic acid
10-nitrolinoleic acid
(9e,12z)-10-nitrooctadeca-9,12-dienoic acid
10-nitro-9-cis,12-cis-octadecadienoate
774603-04-2
9,12-octadecadienoicacid, 10-nitro-, (9e,12z)-
10-nitro-9z,12z-octadecadienoic acid
CHEBI:34125
SCHEMBL2370110
10-nitro-9,12-octadecadienoic acid
lno2
12-nitro-9,12-octadecadienoate
10-nitro-9,12-octadecadienoate
Q27115831
12-nitro-9,12-octadecadienoic acid
LELVHAQTWXTCLY-XYWKCAQWSA-N
DTXSID201261386
(9e,12z)-10-nitro-9,12-octadecadienoic acid
HY-113473
(9e,12z)-10-nitrooctadecadienoic acid
CS-0062333
PD018281
AKOS040756041

Class	Description
nitro fatty acid	Any nitrogen-containing fatty acid that is fatty acid containing at least one nitro group.
octadecadienoic acid	Any straight-chain, C18 polyunsaturated fatty acid having two C=C double bonds.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	14 (58.33)	29.6817
2010's	9 (37.50)	24.3611
2020's	1 (4.17)	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	24 (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
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.04	1	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.45	2	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.06	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
alkenes [no description available]	2.74	3
decamethrin decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure	2.1	1	aromatic ether; cyclopropanecarboxylate ester; nitrile; organobromine compound	agrochemical; antifeedant; calcium channel agonist; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; pyrethroid ester insecticide
rosiglitazone [no description available]	2.05	1	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
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
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2.46	2	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2.1	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
2,3,4-tri-o-acetylarabinopyranosyl isothiocyanate 2,3,4-tri-O-acetylarabinopyranosyl isothiocyanate: RN given refers to (alpha-D)-isomer	2.1	1
octadecadienoic acid octadecadienoic acid: location of unsaturation not specified. octadecadienoate : A long-chain, unsaturated fatty acid anion formed by deprotonation of the carboxy group of any octadecadienoic acid; major species at pH 7.3.. octadecadienoic acid : Any straight-chain, C18 polyunsaturated fatty acid having two C=C double bonds.	2.02	1
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.41	1	cysteinium	fundamental metabolite
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.02	1	1,2-diacyl-sn-glycero-3-phosphocholine
10-nitro-oleic acid 10-nitro-oleic acid: structure in first source. (9E)-10-nitrooctadecenoic acid : A nitro fatty acid that is (9E)-octadec-9-enoic (elaidic) acid substituted by a nitro group at position 10.	2.75	3	long-chain fatty acid; monounsaturated fatty acid; nitro fatty acid	human metabolite
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.02	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
pyrethrins [no description available]	2.1	1
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.45	2	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
2,2'-(hydroxynitrosohydrazono)bis-ethanamine 2,2'-(hydroxynitrosohydrazono)bis-ethanamine: a nitric oxide (NO) generating compound. 1,1-bis(2-aminoethyl)-2-hydroxy-3-oxotriazane : A nitroso compound that is triazane in which the the nitrogen at position 1 is substituted by two 2-aminoethyl groups, that at position 2 is substituted by a hydroxy group, and that at position 3 is substituted by an oxo group.	2.04	1
8-bromocyclic gmp 8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.	2.04	1	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist
8-((4-chlorophenyl)thio)cyclic-3',5'-gmp 8-(4-chlorophenylthio)-cGMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP in which the hydrogen at position 2 on the purine fragment is replaced by a 4-chlorophenylthio group.	2.04	1	3',5'-cyclic purine nucleotide; aryl sulfide; organochlorine compound; ribonucleotide	protein kinase agonist

Condition	Relationship Strength	Studies
Atrial Remodeling Long-term changes in the electrophysiological parameters and/or anatomical structures of the HEART ATRIA that result from prolonged changes in atrial rate, often associated with ATRIAL FIBRILLATION or long periods of intense EXERCISE.	2.13	1
Auricular Fibrillation [description not available]	2.13	1
Cirrhosis [description not available]	2.13	1
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	2.13	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.13	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.05	1
Injury, Myocardial Reperfusion [description not available]	2.05	1
Breast Cancer [description not available]	2.05	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.05	1
Blood Pressure, High [description not available]	2.05	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.05	1
Heart Disease, Ischemic [description not available]	2.07	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2.07	1
Atherogenesis [description not available]	2.05	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.05	1
Innate Inflammatory Response [description not available]	2.04	1
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.	2.04	1

10-nitro-9,12-octadecadienoic acid

Description

Cross-References

Synonyms (25)

Drug Classes (2)

Research

Studies (24)

Market Indicators

Research Demand Index: 11.17

Study Types